Author: carl

There’s a particular type of menswear salesperson I’ve encountered throughout my career—the one who, with practiced sincerity and unwavering eye contact, tells you that the $1,200 sport coat you’re considering isn’t really an expense but an “investment.” You know the spiel: “This jacket will last forever,” “You’ll hand this down to your son,” “The cost-per-wear makes it practically free.” I’ve heard it all. Hell, I’ve probably written some version of it dozens of times over the years.

But after watching countless “investment pieces” get relegated to the dark corners of closets or end up selling for pennies on the dollar at consignment shops, I’ve started asking the uncomfortable question: Which menswear items actually are financial investments in the literal sense? Not just high-quality pieces that last a long time (though that’s valuable), but items that genuinely hold or—pipe dream territory—increase in value over time?

To be clear, buying clothes primarily as financial investments is generally terrible strategy. You’re almost always better off putting that money in an index fund than a closet. But for those who love the intersection of style and collecting, there are legitimate categories where the right purchase can maintain or grow its worth while still being wearable. The trick is separating the true investment-grade items from the sales floor mythology.

So I decided to track the actual resale and auction values of high-end menswear over the past decade, consulting with vintage dealers, auction houses, and collectors to identify patterns of what truly appreciates. The results were surprising, often contradicting conventional wisdom and marketing claims.

Let’s start with what definitely isn’t an investment: almost any regular production item from a luxury brand, no matter how well-made. That Brioni suit with the perfect Neapolitan shoulder? The Loro Piana cashmere sweater that feels like wearing a cloud? The meticulously crafted Edward Green oxfords? All spectacular products that might last decades with proper care, but the secondary market value drops 40-60% the moment you remove the tags, and it continues declining from there.

I learned this lesson the hard way when I tried to sell a barely-worn Cucinelli sport coat that I’d convinced myself was “an investment in my professional appearance” when I bought it four years ago. Original price: eye-watering. Consignment offer: soul-crushing. The painful reality is that standard luxury menswear depreciates faster than a new car driving off the lot, regardless of how many hand stitches are involved.

So what actually does maintain or increase value? Let’s break it down by category:

The strongest investment category, by far, is limited production footwear—specifically, certain boots and welted shoes from brands with cult followings. The undisputed king here is Viberg, the Canadian bootmaker whose limited releases often sell out within minutes. Their rarest makeups—particularly those using unique or discontinued leathers—routinely resell for 20-40% above retail. A pair of their “Matte Black Calf” service boots from 2015 that retailed for $720 recently sold for $1,200 on a secondary market, essentially appreciating 10% annually while presumably being worn.

Similarly, certain Alden limited editions show remarkable appreciation. Their collaborations with shops like Leffot, Brick+Mortar, and The Bureau Belfast have proven especially valuable, with some rare shell cordovan models doubling in price over 5-7 years. The most collectible? Their “Cigar” and “Ravello” shell cordovan models, which use increasingly scarce light brown shell. One collector I interviewed has seen his collection of eight rare Alden models appreciate approximately 85% over six years.

The key factors that drive appreciation in footwear are material scarcity (especially rare shell cordovan colors), limited production numbers, and brand prestige within collecting communities rather than in the broader luxury market. Edward Green and John Lobb make objectively finer shoes than either Viberg or Alden, but their secondary values don’t hold nearly as well because they lack the cultish collector base.

Moving to outerwear, certain leather jackets have proven remarkably investment-worthy, though with important caveats. Vintage pieces from American makers like Schott, Aero, and Langlitz from the 1940s-1970s have appreciated steadily, with pristine examples selling for three to five times their inflation-adjusted original prices. A 1950s Schott Perfecto that would have cost around $400 in today’s dollars now easily commands $1,500-2,000 if in excellent condition.

The contemporary leather jacket market is more complicated. Most depreciate heavily, but specific limited editions from artisanal makers have bucked the trend. Ten C’s OJJ (Original Japanese Jersey) pieces maintain about 80-90% of their retail value years after purchase. The Real McCoy’s limited production jackets typically hold steady at close to their retail price, essentially offering “free wear” to the original purchaser who later sells.

The wildcard in leather investments is Bode’s one-of-a-kind pieces, which have shown genuine appreciation in the secondary market. Their hand-embroidered and appliquéd leather jackets that retailed for $1,800-2,500 just three years ago now command $3,000+ on resale platforms. Whether this reflects lasting value or just the current hype around the brand remains to be seen.

Denim presents a fascinating investment case study with tremendous variance. Standard production jeans, even from prestigious Japanese selvedge makers, typically lose 20-40% of their value immediately, then stabilize. However, certain limited collaborative releases show remarkable appreciation.

The most notable example is the Iron Heart “25oz” anniversary series, which has appreciated 50-100% depending on the specific model. Similarly, Samurai Jeans’ limited-run natural indigo pieces have consistently maintained or increased their value. These aren’t small amounts, either—we’re talking about jeans that originally retailed for $300-500 now selling for $600-1,000 in worn but well-maintained condition.

The strongest denim investments come from brands that have either closed or significantly changed their production methods. Warehouse Japan’s early “tonal” stitched models from the early 2000s now sell for 2-3x their original price. Original Full Count jeans made while founder Mikiharu Tsujita was still directly overseeing production command similar premiums.

The most dramatic denim appreciation comes from collaborative or small-batch releases that somehow capture a moment in denim culture. The Studio D’Artisan “Cobra” models, The Flat Head “Red Edge” commemorative jeans, and the Strike Gold “Mud” denim series have all at least doubled in value since their initial release, with particularly rare sizes seeing even stronger appreciation.

Watches are well-known investment vehicles, but the findings here run counter to common assumptions. The mega-luxury brands like Rolex, Patek Philippe, and Audemars Piguet have indeed seen spectacular appreciation over the past decade, but this appears increasingly bubble-like and concentrated in specific models. More relevant to the average menswear enthusiast are the more accessible watch investments that have consistently performed well.

Universal Genève chronographs from the 1960s-70s have shown steady 10-15% annual appreciation over the past decade. Certain Seiko limited editions—particularly the “Alpinist” variants and specific Grand Seiko limited production models—have doubled or tripled in value over a similar timeframe. The key factors appear to be limited production numbers, design distinctiveness, and movements that are no longer produced.

The surprising dark horse in watch investments has been certain Swatch limited editions, particularly artist collaborations from the 1980s and early ’90s. Some of these plastic watches that originally retailed for $50-75 now command $500-1,000 from collectors. A Keith Haring collaboration Swatch from 1986 that sold for $50 now trades for upwards of $7,000 in new-old-stock condition—a return that would make Warren Buffett jealous.

In tailored clothing, the investment picture is almost universally bleak, with one notable exception: bespoke suits with prestigious provenance. Savile Row garments made for celebrities or historical figures have shown remarkable appreciation at auction. A Henry Poole suit made for a British duke in the 1920s sold for £12,000 at Bonhams in 2018—roughly ten times what a similar commission would have cost at the time. However, this applies only to pieces with documented famous ownership, not to the average bespoke commission.

Knitwear follows a similar pattern to tailoring—almost universally poor investment potential with extremely narrow exceptions. Certain discontinued Fair Isle patterns from heritage makers like Jamieson’s of Shetland have appreciated moderately (20-30% over a decade). The only genuine knitwear investments I’ve identified are original hand-knits from the Cowichan First Nation from the 1950s-1970s, which have seen steady appreciation as their cultural significance has become more widely recognized. These distinctive sweaters that originally sold for the equivalent of $100-200 now routinely fetch $500-1,000 at vintage dealers.

The wild world of sneakers deserves its own article (or book), but it’s worth noting that despite the headline-grabbing prices for rarities, most “investment grade” sneakers actually produce negative returns after accounting for authentication costs, selling fees, storage, and inflation. The exceptions are primarily extremely limited collaborations and certain original releases from the 1980s kept in deadstock condition.

Now for the broad categories that have shown almost no investment potential: dress shirts, neckties, casual shirts, and most accessories. Even the most prestigious makers see their products lose 60-80% of value immediately upon purchase. The lone exception I’ve found is certain vintage Ralph Lauren ties from the 1980s and early ’90s, particularly hand-block printed patterns that are no longer produced. These occasionally sell for slight premiums over their inflation-adjusted original prices, but hardly enough to justify their purchase as investments.

So what patterns emerge from these findings? The characteristics that contribute to menswear actually appreciating in value are remarkably consistent:

Limited production is essential but not sufficient. Just because something is rare doesn’t mean it will appreciate. The scarcity needs to be authentic (tied to material constraints or deliberate artistic choices) rather than artificially created for marketing purposes.

Cultural significance matters tremendously. Items that somehow embody or represent a particular moment or movement in menswear history appreciate far more than technically superior products without cultural resonance. This explains why certain Japanese denim from the “golden age” of reproduction appreciation continues appreciating while objectively “better” contemporary jeans don’t.

Craft processes that can’t be replicated drive value. When skilled artisans retire, when techniques become economically unfeasible, or when source materials become unavailable, the products created during these unique windows often appreciate significantly.

Documentation and provenance create premium value. The leather jacket with proof it was worn by McQueen’s stunt double, the suit with handwritten measurements for a famous politician—these stories attached to garments create value far beyond the item’s intrinsic quality.

The most surprising finding? Price point has relatively little correlation with investment potential. Some of the strongest-performing investments (vintage Swatch watches, certain Seiko models, early American workwear) started at accessible price points, while many ultra-luxury items depreciate catastrophically.

So what does this mean for the average style enthusiast? First, stop kidding yourself that your regular clothing purchases are investments. They’re expenses—hopefully worthwhile ones that bring quality and joy to your life, but expenses nonetheless. If you’re buying primarily for appreciation, you’re in the wrong market entirely.

However, if you’re passionate about certain categories and learn their nuances, there are genuine opportunities to wear beautiful things that maintain or increase their value. The best approach combines passion with selective purchasing—focusing on limited releases with genuine production constraints, historical significance, or craft elements that cannot be reproduced.

My personal strategy has evolved toward what I call “neutralizing” rather than “investing”—focusing on items that I genuinely love and want to wear, but that have characteristics suggesting they’ll hold reasonable value. This means I can enjoy them for years, then likely recoup a significant portion of my purchase price if my tastes or needs change. I’ve found this approach infinitely more satisfying than treating clothes as pure investment vehicles.

The most successful collectors I interviewed for this article shared a common philosophy: they buy what they genuinely love and know deeply, with appreciation being a pleasant side effect rather than the primary motivation. The retired banker with 60+ pairs of shell cordovan Aldens didn’t set out to build an appreciating asset—he simply loved the specific aesthetic and quality they represented. That his collection is now worth substantially more than he paid is a bonus to the years of enjoyment they’ve provided.

And that might be the most important insight of all—the best “investment” in menswear isn’t financial but experiential. The garments that give you confidence, joy, and functionality in your daily life provide returns that no spreadsheet can capture. If they happen to maintain some financial value along the way, consider it a bonus—like finding an unexpected twenty in last winter’s coat pocket, but hopefully with a few more zeros attached.

It started as a joke over Sunday brunch. Megan was giving me that look—the one that says “I love you but what the hell are you wearing?”—as I sat across from her in what I thought was a perfectly acceptable combination of faded jeans and a vintage flannel I’d scored at a thrift shop in Williamsburg. I was defending my choices, as I always do, with my standard line about how menswear experts appreciate “considered dishevelment” when she put down her mimosa and said, “You know what would be funny? If you let me dress you for a week. Just to see what happens.”

Now, I should mention that my girlfriend works in PR for a luxury fashion brand. She spends her days surrounded by people who treat getting dressed like it’s performance art. Meanwhile, I write about men’s style for a living but have somehow cultivated what my boss once diplomatically called my “specific aesthetic”—a mix of classic menswear, vintage finds, and the occasional questionable experiment. I’m the guy who will pair a $900 sport coat with ten-year-old New Balances and think it’s the perfect high-low mix. Megan calls it my “professionally rumpled professor vibe.”

“Absolutely not,” I told her, spearing a piece of avocado toast. “There’s a conflict of interest here. I literally get paid to have opinions about men’s clothes.”

“Exactly,” she said, that mischievous glint in her eye. “Think of it as research. You’re always writing about guys stepping outside their comfort zones. When’s the last time you actually did that yourself?”

She had me there. The truth is, I’ve settled into my style over the years. I know what works for me—or at least what I think works for me—and I’ve built a wardrobe around those principles. The idea of surrendering that control was genuinely uncomfortable. Which, of course, meant I had to do it.

“Fine,” I said, already regretting it. “One week. But I get veto power if you try to put me in skinny jeans or anything with sequins.”

“Deal,” she said, clinking her glass against mine. “And no vetoes. That defeats the entire purpose.”

That night, Megan went through my closet like an archaeologist examining artifacts from a particularly unfashionable civilization. “How many blue Oxford shirts does one man need?” she asked, pushing hangers aside with increasing concern. “And why do you have the same gray sweater in what appears to be three slightly different shades of gray?”

“They’re completely different!” I protested. “That one’s charcoal, that’s slate, and the other is more of a heathered—”

“This is worse than I thought,” she interrupted, pulling out her phone to take notes. “I’m going to need to bring in some reinforcements.”

The “reinforcements” turned out to be a few pieces borrowed from her brother Michael (who, annoyingly, dresses like an Italian movie star despite working as an accountant) and two strategic purchases she insisted were “investments” rather than expenses. I tried not to wince when she came home with shopping bags. The experiment was getting expensive before it even started.

Monday morning arrived, and with it, the first outfit. Megan had laid it out on the bed like I was a kid on the first day of school: slim-cut navy chinos (mine, thankfully), a light blue button-up that I didn’t hate, and—here was the twist—a burgundy knit tie that I’d owned for years but rarely wore, plus a camel-colored cardigan instead of my usual navy blazer. The shoes were brown suede chukkas that had been sitting unworn in my closet since an ill-advised shopping spree three years ago.

“This isn’t that different from what I’d normally wear,” I said, relieved.

“Exactly,” she replied. “We’re starting with the shallow end before I throw you into the deep. But notice there’s no tweed, nothing frayed, and—most importantly—it all actually fits you properly.”

I rolled my eyes but got dressed. The pants were admittedly more flattering than my usual slightly-too-loose chinos. The cardigan felt soft and looked richer than my standard navy jacket. Looking in the mirror, I had to admit I looked more put-together than usual, though I’d never say that out loud.

Walking into the Style Authority office, I braced myself for comments. Our fashion team notices everything—a new haircut, different glasses, the slightest tweak to your usual look. Sure enough, Trevor from the digital team stopped mid-sip of his cold brew.

“New cardigan?” he asked, eyebrow raised. “Looks good, man. Very Brunello Cucinelli catalog.”

I mumbled something about “trying something different” and hurried to my desk, both pleased and slightly annoyed by the attention. But the real surprise came during the editorial meeting when our editor-in-chief, Daniel, actually stopped mid-sentence while discussing upcoming features to say, “Reed, you look especially sharp today. Like you’re actually taking your own advice for once.”

The office erupted in laughter. I felt my face flush but gave a little mock bow. “Thank my girlfriend,” I said. “She’s staging an intervention.”

Tuesday’s outfit pushed me further out of my comfort zone: gray dress pants (fitted more narrowly than I’d choose myself), a white Oxford (mine), a black knit blazer that felt surprisingly comfortable, and—the real shock—a pair of sleek black Chelsea boots I’d never have picked out myself. The overall effect was more modern, more metropolitan than my usual vintage-inspired look.

“You look like you’re going to fire someone,” said my colleague Lisa when I walked in. “But in a hot way.”

The strangest part was how differently people at work seemed to interact with me. Junior writers who normally just waved in passing stopped to ask my opinion on pitches. The marketing guy who’d been avoiding my emails about collaboration suddenly materialized at my desk, coffee in hand, ready to talk strategy. Even the front desk security guard gave me a “Looking sharp, Mr. Reed” instead of the usual nod.

I texted Megan at lunch: “People are acting weird. I think you’ve turned me into Patrick Bateman.”

She replied with a laughing emoji and: “That’s just how people treat guys who look like they have their shit together.”

Wednesday’s look nearly broke me. Megan had pulled out a pair of olive green pants that were—and there’s no gentle way to put this—significantly more fitted than I’d normally wear. “These are basically skinny jeans,” I protested as I struggled to get them on.

“They’re just regular pants that actually fit,” she countered. “Most men wear everything two sizes too big. You’re drowning in fabric half the time.”

She paired them with a simple black t-shirt (admittedly the softest one I’ve ever worn—some Japanese brand I’d never heard of), a light gray unstructured blazer, and clean white sneakers. The overall effect was roughly 70% more fashionable than I’d normally dress, and about 40% less comfortable—at least psychologically.

I felt self-conscious walking into the office, certain I looked like I was trying too hard. But something interesting happened. Rather than mockery, I received genuine compliments. The senior style editor—a guy who regularly attends Paris Fashion Week and once made an intern cry by criticizing his loafers—actually stopped me in the hallway.

“This is a good direction for you,” he said, gesturing vaguely at my outfit. “More contemporary. You should consider featuring this kind of look in your column.”

The real surprise came that afternoon when Daniel called me into his office. I assumed it was about the feature I was working on for the September issue. Instead, he closed the door and offered me a promotion—style director for the print magazine in addition to my digital role. It came with a not-insignificant raise and considerably more influence over the publication’s visual direction.

“I’ve been thinking about this for a while,” he said, “but seeing you freshen up your look this week convinced me you’re ready to help guide our overall aesthetic. You understand classic style but aren’t stuck in the past.”

I walked out of his office in a daze and immediately called Megan.

“You’re not going to believe what just happened,” I told her.

“Your boss finally realized you’re brilliant?” she asked.

“My boss gave me a promotion and specifically mentioned my outfit. What kind of twisted social experiment are you running here?”

She laughed. “I told you clothes matter! And you write about this for a living!”

Thursday and Friday continued the experiment. Thursday was a monochromatic look—all black everything, from jeans to t-shirt to bomber jacket—which felt simultaneously out of character and ridiculously easy to pull off. Friday was what Megan called “elevated casual”: dark jeans, a washed chambray shirt, and a textured sport coat in a subtle check pattern that I actually owned but rarely wore.

By Friday afternoon, I’d received more compliments on my appearance in a single week than in the previous six months combined. A senior editor from GQ who was visiting our office for a collaboration actually asked where I’d gotten my jacket. My neighbor in the elevator, who’d never spoken to me before despite living on the same floor for two years, struck up a conversation. The barista at my regular coffee shop gave me a free pastry “just because.” The world was treating a slightly-better-dressed version of me noticeably better.

Over dinner Friday night, I reluctantly debriefed with Megan.

“Fine, I admit it,” I said, sipping my bourbon. “The experiment worked. People responded differently. But isn’t that a little depressing? That something as superficial as slightly more fitted pants could change how I’m perceived professionally?”

Megan considered this, twirling pasta around her fork. “I don’t think it’s that they like you better because you’re more stylish. I think it’s that you were telegraphing something different about yourself. More current, more adaptable, more aware of how you’re presenting. Those are qualities people respond to in any context.”

She had a point. And the truth is, by Friday I wasn’t even feeling self-conscious anymore. The slightly more tailored fit, the contemporary silhouettes—they had started to feel normal. Comfortable, even.

“So,” she said, “what did you learn from this very scientific experiment?”

I thought about it. “That my girlfriend is annoyingly right sometimes. That people—even style professionals—judge books by their covers more than they admit. That I’ve been playing it safe with my own style while telling readers to take risks. And that a good tailor is worth their weight in gold.”

She smiled. “And?”

“And I’m keeping the Chelsea boots. They make me feel tall.”

The following Monday, left to my own devices, I stood before my closet pondering what to wear. I reached for my usual uniform—well-worn chinos, Oxford shirt, tweed jacket—then hesitated. Instead, I grabbed the olive pants, paired them with a white Oxford and the gray blazer, then added a patterned pocket square that Megan had introduced to the mix.

Looking in the mirror, I saw a version of myself that felt both familiar and refreshed. Not a total style overhaul, but an evolution. A slightly more current take on my personal aesthetic.

I texted Megan a mirror selfie before heading out the door. Her response came seconds later: “Look who’s a quick study. But we need to talk about that pocket square folding technique…”

Some habits die hard. But I’ve kept the promotion, the boots, and the slightly more fitted pants. And I’ve gained a new perspective for my column—sometimes the person who most needs a style intervention is the one giving the advice. Now excuse me while I go write about the transformative power of letting someone else dress you. After I change into something my girlfriend would approve of, of course.

My apartment has a closet problem. Specifically, I don’t have enough closets to contain my borderline problematic shoe collection. At last count, I own 31 pairs—ranging from handmade Italian dress shoes I’ve worn exactly twice to beat-up Vans that should have been retired during the Obama administration but somehow keep surviving because they’re “perfectly broken in” (read: one step away from disintegrating).

The irony isn’t lost on me. I regularly advise readers to invest in fewer, better things, all while maintaining a footwear arsenal that could outfit a small village. When my friend Marcus visited last month, he stared at my shoe rack—which had long ago overflowed into a “temporary” line along my bedroom wall—and asked the most damning question possible: “Dude, how many of these do you actually wear?”

The answer was humbling. Of the 31 pairs, I regularly wore maybe seven. The rest sat in various states of neglect, some still pristine in their boxes, others worn a handful of times before being relegated to the land of good intentions and poor impulse control.

This realization led me to a thought experiment: If I had to start from zero, what’s the absolute minimum number of shoes a man actually needs? Not wants, not “would be nice to have for that specific situation that might come up twice a year,” but genuinely needs to cover 99% of life situations.

After considerable soul-searching (and sole-searching—sorry, couldn’t resist), I’ve arrived at the essential five. Just five pairs of shoes that can handle everything from weddings to workouts, business meetings to backyard barbecues. And no, this isn’t some arbitrary number I chose to make a catchy headline—I genuinely believe these five categories cover the full spectrum of what American men actually need on their feet.

Now, a quick disclaimer before the shoe minimalists come after me: Yes, you could technically get by with fewer. My grandfather famously owned only two pairs of shoes his entire adult life—black oxfords for church and work boots for everything else. He also walked eight miles to school uphill both ways, or so the story goes. But for modern men balancing work, social lives, and some semblance of physical activity, five pairs hits the sweet spot of versatility without excess.

So here they are—the only five shoes American men actually need:

**1. The Brown Leather Derby**

If I could only recommend one shoe to every man in America, it would be a medium-to-dark brown derby in a classic round toe shape. Not an oxford (too formal for many situations), not a brogue (too busy for some settings), and definitely not black (too severe with casual clothing). A simple, clean brown derby is the closest thing to a perfect all-purpose shoe ever created.

Why a derby specifically? The open lacing system (where the eyelet tabs are sewn on top of the vamp) creates a slightly more relaxed look than an oxford, making it appropriate for everything from business meetings to dinner dates to semi-formal events. In the right shade of brown, it works with navy suits, gray trousers, chinos, and even dark jeans.

I’ve had my Allen Edmonds Boulevards in dark chili for seven years now, resoled twice, and they still look better with each wear. They’ve handled boardroom presentations, wedding receptions (though not as a groomsman), first dates, job interviews, and even a surprisingly formal funeral where I realized en route that I’d forgotten to pack my black oxfords.

Price point here matters less than quality construction. Anything from Meermin ($195) to Grant Stone ($350) to Alden ($550) will serve you well if properly maintained. The key is Goodyear welting for resoling, quality full-grain leather that will patinate beautifully, and a timeless round toe shape that won’t look dated when styles shift.

**2. The Minimalist White Sneaker**

In our increasingly casual world, a clean white sneaker has gone from weekend option to weekday essential. The right white sneaker now works with everything from shorts to suits, making it perhaps the most versatile shoe in a contemporary man’s rotation.

The key here is simplicity. You want minimal branding, clean lines, and no unnecessary design elements. This isn’t about chasing trends or specific brands—it’s about finding a sneaker that won’t look dated in 18 months. The prototype is the Common Projects Achilles Low, which created the modern archetype of the minimalist white sneaker, but there are excellent options at every price point from Veja ($145) to Greats ($180) to Crown Northampton ($390) if you want something handmade.

My own white sneakers of choice are Gustin’s version, which I’ve had for four years and have developed a patina that somehow makes them look better with age—something I didn’t think was possible with white leather. I’ve worn them with everything from casual suits at summer weddings to jeans and a t-shirt for weekend coffee runs. They’ve even handled lightweight hiking when I misjudged a “casual nature walk” that turned into a four-mile trail.

The trick with white sneakers is accepting that they won’t stay pristine, nor should they. A little character builds over time, and there’s something deeply satisfying about sneakers that tell a story rather than looking box-fresh. That said, regular cleaning and shoe trees will extend their life significantly.

**3. The Weather Boot**

Every man needs at least one pair of boots that can handle whatever Mother Nature throws at them without looking like you’re about to summit Everest. This is where many men go wrong—either wearing delicate dress boots in inappropriate conditions or clomping around in overbuilt tactical boots that look ridiculous with normal clothes.

The sweet spot is what I call the “weather boot”—substantial enough to handle rain, light snow, and rough terrain, but sleek enough to wear with jeans or chinos without looking like you’re lost on your way to a construction site.

For most American climates, a Goodyear-welted leather boot with a rubber or Dainite sole hits this balance perfectly. Red Wing’s Iron Ranger with a Vibram mini-lug sole, Alden’s Indy boot, Grant Stone’s Diesel Boot, or Thursday’s Captain all fit the bill at various price points. The key is finding something water-resistant (through either the leather or treatment), with enough traction to handle slippery conditions, but clean enough in design to work in casual social settings.

My personal weather boots are Truman’s in waxy commander leather—essentially a waxed flesh-out construction that handles water beautifully while developing fantastic character. They’ve survived Chicago slush, Seattle downpours, and somehow still clean up well enough for casual Friday at the office.

The weather boot should be your go-to from roughly October through April in most climates, handling everything from rainy commutes to weekend hikes to bar outings when the forecast looks questionable. In truly extreme weather you might need dedicated snow boots, but for 95% of foul-weather situations, a good weather boot has you covered.

**4. The Athletic Performer**

The days of wearing one pair of cross-trainers for every athletic endeavor are, thankfully, behind us. However, the opposite problem now exists—specialized shoes for every conceivable activity, from trail running to HIIT classes to pickleball. Unless you’re a serious athlete in a specific discipline, this level of specialization is completely unnecessary.

What most men actually need is one pair of true performance athletic shoes designed for their primary form of exercise. For many, this means running shoes, but it could be training shoes for gym work, court shoes for tennis/basketball, or even approach shoes for hiking.

The key is honest assessment—what physical activity do you actually do regularly, not what you aspire to do? Then invest in one quality pair specifically designed for that purpose.

I primarily run and do HIIT workouts, so my athletic shoes are Brooks Ghosts—not the sexiest choice, but they handle both activities competently while providing the support my problematic knees require. They aren’t fashion statements, nor should they be. This is the one category where function absolutely trumps form.

One important note: your athletic shoes should be used exclusively for their intended purpose. They are tools, not fashion accessories, and using performance shoes for casual wear not only looks awkward but dramatically shortens their effective life by compressing the supportive materials when they’re not needed.

**5. The Summer-Weight Option**

The fifth essential pair addresses a specific seasonal need—something breathable for the hottest months when leather sticks to your feet and even the lightest sneakers feel oppressive. What this specific shoe looks like depends somewhat on your personal style and local climate, but the category itself is non-negotiable.

For most men, this means either a high-quality canvas sneaker (think Converse, Vans, or Sperry) or a proper loafer in suede or unlined leather. The key is lightness, breathability, and the ability to be worn sockless (or with no-show socks for the more hygienically minded among us).

My summer shoe of choice is an unlined suede loafer—specifically, Alden’s unlined leisure handsewers in snuff suede, which have molded to my feet like slippers while still looking presentable enough for all but the most formal summer occasions. In brutal New York August heat, they’re the only shoes that don’t feel like foot saunas after an hour of walking.

The summer shoe should be able to handle everything from shorts to linen trousers, beach outings to outdoor dining. It’s the footwear equivalent of your favorite summer shirt—comfortable, relaxed, but still put-together.

**What About Formal Occasions?**

The observant reader might notice I haven’t included a dedicated formal shoe like a black oxford. This is deliberate. For the vast majority of American men, formal events requiring black shoes occur so infrequently (often just weddings and funerals) that dedicating precious closet space to shoes worn perhaps twice a year makes little sense.

For most formal occasions that aren’t black tie, a well-polished dark brown derby (shoe #1 in our essential five) will handle the situation perfectly well. If you attend black tie events regularly or work in an ultra-conservative field like certain areas of law or finance, then yes, black oxfords become a sixth essential. But for the other 95% of men, they’re an unnecessary addition that will sit unworn most of the time.

**The Implementation Plan**

Now, I’m not suggesting you trash your existing collection and immediately buy these five pairs. That would be both financially irresponsible and environmentally wasteful. Instead, use this framework to guide future purchases and replacements. As your current shoes wear out, consider whether their replacements should align with one of these essential categories before adding anything new.

For those building a wardrobe from scratch (or recovering from a major closet purge), prioritize based on your lifestyle. If you work in a business casual environment, start with the derby and white sneaker. If you’re outdoors frequently, the weather boot might jump to the top of the list.

The beauty of this framework is its adaptability to your specific needs while maintaining the discipline of true essentialism. These five archetypes cover practically every situation the modern man encounters, from the boardroom to the bar to the ballgame.

As for me? I’ve begun the painful process of culling my collection, keeping only those pairs that serve a genuine purpose or have significant sentimental value (like the oxblood loafers I wore when I received my first major journalism award). The overflow shoe rack is gone, and I’ve discovered something unexpected in the process—getting dressed is actually easier with fewer options. Decision fatigue is real, even with something as seemingly trivial as footwear.

Will I ever get down to just five pairs? Probably not. The professional hazard of being a style writer means I’ll always have a few extra options for testing and research purposes. But I’ve found tremendous clarity in recognizing the difference between what I need and what I merely want. And in a consumer culture constantly telling us that more is better, sometimes the most rebellious act is deciding that enough is actually enough.

My apartment has a closet problem. Specifically, I don’t have enough closets to contain my borderline problematic shoe collection. At last count, I own 31 pairs—ranging from handmade Italian dress shoes I’ve worn exactly twice to beat-up Vans that should have been retired during the Obama administration but somehow keep surviving because they’re “perfectly broken in” (read: one step away from disintegrating).

The irony isn’t lost on me. I regularly advise readers to invest in fewer, better things, all while maintaining a footwear arsenal that could outfit a small village. When my friend Marcus visited last month, he stared at my shoe rack—which had long ago overflowed into a “temporary” line along my bedroom wall—and asked the most damning question possible: “Dude, how many of these do you actually wear?”

The answer was humbling. Of the 31 pairs, I regularly wore maybe seven. The rest sat in various states of neglect, some still pristine in their boxes, others worn a handful of times before being relegated to the land of good intentions and poor impulse control.

This realization led me to a thought experiment: If I had to start from zero, what’s the absolute minimum number of shoes a man actually needs? Not wants, not “would be nice to have for that specific situation that might come up twice a year,” but genuinely needs to cover 99% of life situations.

After considerable soul-searching (and sole-searching—sorry, couldn’t resist), I’ve arrived at the essential five. Just five pairs of shoes that can handle everything from weddings to workouts, business meetings to backyard barbecues. And no, this isn’t some arbitrary number I chose to make a catchy headline—I genuinely believe these five categories cover the full spectrum of what American men actually need on their feet.

Now, a quick disclaimer before the shoe minimalists come after me: Yes, you could technically get by with fewer. My grandfather famously owned only two pairs of shoes his entire adult life—black oxfords for church and work boots for everything else. He also walked eight miles to school uphill both ways, or so the story goes. But for modern men balancing work, social lives, and some semblance of physical activity, five pairs hits the sweet spot of versatility without excess.

So here they are—the only five shoes American men actually need:

**1. The Brown Leather Derby**

If I could only recommend one shoe to every man in America, it would be a medium-to-dark brown derby in a classic round toe shape. Not an oxford (too formal for many situations), not a brogue (too busy for some settings), and definitely not black (too severe with casual clothing). A simple, clean brown derby is the closest thing to a perfect all-purpose shoe ever created.

Why a derby specifically? The open lacing system (where the eyelet tabs are sewn on top of the vamp) creates a slightly more relaxed look than an oxford, making it appropriate for everything from business meetings to dinner dates to semi-formal events. In the right shade of brown, it works with navy suits, gray trousers, chinos, and even dark jeans.

I’ve had my Allen Edmonds Boulevards in dark chili for seven years now, resoled twice, and they still look better with each wear. They’ve handled boardroom presentations, wedding receptions (though not as a groomsman), first dates, job interviews, and even a surprisingly formal funeral where I realized en route that I’d forgotten to pack my black oxfords.

Price point here matters less than quality construction. Anything from Meermin ($195) to Grant Stone ($350) to Alden ($550) will serve you well if properly maintained. The key is Goodyear welting for resoling, quality full-grain leather that will patinate beautifully, and a timeless round toe shape that won’t look dated when styles shift.

**2. The Minimalist White Sneaker**

In our increasingly casual world, a clean white sneaker has gone from weekend option to weekday essential. The right white sneaker now works with everything from shorts to suits, making it perhaps the most versatile shoe in a contemporary man’s rotation.

The key here is simplicity. You want minimal branding, clean lines, and no unnecessary design elements. This isn’t about chasing trends or specific brands—it’s about finding a sneaker that won’t look dated in 18 months. The prototype is the Common Projects Achilles Low, which created the modern archetype of the minimalist white sneaker, but there are excellent options at every price point from Veja ($145) to Greats ($180) to Crown Northampton ($390) if you want something handmade.

My own white sneakers of choice are Gustin’s version, which I’ve had for four years and have developed a patina that somehow makes them look better with age—something I didn’t think was possible with white leather. I’ve worn them with everything from casual suits at summer weddings to jeans and a t-shirt for weekend coffee runs. They’ve even handled lightweight hiking when I misjudged a “casual nature walk” that turned into a four-mile trail.

The trick with white sneakers is accepting that they won’t stay pristine, nor should they. A little character builds over time, and there’s something deeply satisfying about sneakers that tell a story rather than looking box-fresh. That said, regular cleaning and shoe trees will extend their life significantly.

**3. The Weather Boot**

Every man needs at least one pair of boots that can handle whatever Mother Nature throws at them without looking like you’re about to summit Everest. This is where many men go wrong—either wearing delicate dress boots in inappropriate conditions or clomping around in overbuilt tactical boots that look ridiculous with normal clothes.

The sweet spot is what I call the “weather boot”—substantial enough to handle rain, light snow, and rough terrain, but sleek enough to wear with jeans or chinos without looking like you’re lost on your way to a construction site.

For most American climates, a Goodyear-welted leather boot with a rubber or Dainite sole hits this balance perfectly. Red Wing’s Iron Ranger with a Vibram mini-lug sole, Alden’s Indy boot, Grant Stone’s Diesel Boot, or Thursday’s Captain all fit the bill at various price points. The key is finding something water-resistant (through either the leather or treatment), with enough traction to handle slippery conditions, but clean enough in design to work in casual social settings.

My personal weather boots are Truman’s in waxy commander leather—essentially a waxed flesh-out construction that handles water beautifully while developing fantastic character. They’ve survived Chicago slush, Seattle downpours, and somehow still clean up well enough for casual Friday at the office.

The weather boot should be your go-to from roughly October through April in most climates, handling everything from rainy commutes to weekend hikes to bar outings when the forecast looks questionable. In truly extreme weather you might need dedicated snow boots, but for 95% of foul-weather situations, a good weather boot has you covered.

**4. The Athletic Performer**

The days of wearing one pair of cross-trainers for every athletic endeavor are, thankfully, behind us. However, the opposite problem now exists—specialized shoes for every conceivable activity, from trail running to HIIT classes to pickleball. Unless you’re a serious athlete in a specific discipline, this level of specialization is completely unnecessary.

What most men actually need is one pair of true performance athletic shoes designed for their primary form of exercise. For many, this means running shoes, but it could be training shoes for gym work, court shoes for tennis/basketball, or even approach shoes for hiking.

The key is honest assessment—what physical activity do you actually do regularly, not what you aspire to do? Then invest in one quality pair specifically designed for that purpose.

I primarily run and do HIIT workouts, so my athletic shoes are Brooks Ghosts—not the sexiest choice, but they handle both activities competently while providing the support my problematic knees require. They aren’t fashion statements, nor should they be. This is the one category where function absolutely trumps form.

One important note: your athletic shoes should be used exclusively for their intended purpose. They are tools, not fashion accessories, and using performance shoes for casual wear not only looks awkward but dramatically shortens their effective life by compressing the supportive materials when they’re not needed.

**5. The Summer-Weight Option**

The fifth essential pair addresses a specific seasonal need—something breathable for the hottest months when leather sticks to your feet and even the lightest sneakers feel oppressive. What this specific shoe looks like depends somewhat on your personal style and local climate, but the category itself is non-negotiable.

For most men, this means either a high-quality canvas sneaker (think Converse, Vans, or Sperry) or a proper loafer in suede or unlined leather. The key is lightness, breathability, and the ability to be worn sockless (or with no-show socks for the more hygienically minded among us).

My summer shoe of choice is an unlined suede loafer—specifically, Alden’s unlined leisure handsewers in snuff suede, which have molded to my feet like slippers while still looking presentable enough for all but the most formal summer occasions. In brutal New York August heat, they’re the only shoes that don’t feel like foot saunas after an hour of walking.

The summer shoe should be able to handle everything from shorts to linen trousers, beach outings to outdoor dining. It’s the footwear equivalent of your favorite summer shirt—comfortable, relaxed, but still put-together.

**What About Formal Occasions?**

The observant reader might notice I haven’t included a dedicated formal shoe like a black oxford. This is deliberate. For the vast majority of American men, formal events requiring black shoes occur so infrequently (often just weddings and funerals) that dedicating precious closet space to shoes worn perhaps twice a year makes little sense.

For most formal occasions that aren’t black tie, a well-polished dark brown derby (shoe #1 in our essential five) will handle the situation perfectly well. If you attend black tie events regularly or work in an ultra-conservative field like certain areas of law or finance, then yes, black oxfords become a sixth essential. But for the other 95% of men, they’re an unnecessary addition that will sit unworn most of the time.

**The Implementation Plan**

Now, I’m not suggesting you trash your existing collection and immediately buy these five pairs. That would be both financially irresponsible and environmentally wasteful. Instead, use this framework to guide future purchases and replacements. As your current shoes wear out, consider whether their replacements should align with one of these essential categories before adding anything new.

For those building a wardrobe from scratch (or recovering from a major closet purge), prioritize based on your lifestyle. If you work in a business casual environment, start with the derby and white sneaker. If you’re outdoors frequently, the weather boot might jump to the top of the list.

The beauty of this framework is its adaptability to your specific needs while maintaining the discipline of true essentialism. These five archetypes cover practically every situation the modern man encounters, from the boardroom to the bar to the ballgame.

As for me? I’ve begun the painful process of culling my collection, keeping only those pairs that serve a genuine purpose or have significant sentimental value (like the oxblood loafers I wore when I received my first major journalism award). The overflow shoe rack is gone, and I’ve discovered something unexpected in the process—getting dressed is actually easier with fewer options. Decision fatigue is real, even with something as seemingly trivial as footwear.

Will I ever get down to just five pairs? Probably not. The professional hazard of being a style writer means I’ll always have a few extra options for testing and research purposes. But I’ve found tremendous clarity in recognizing the difference between what I need and what I merely want. And in a consumer culture constantly telling us that more is better, sometimes the most rebellious act is deciding that enough is actually enough.

Let me set the scene: It’s a Tuesday afternoon, I’m on deadline for three different articles, and my editor texts asking if I can cover a last-minute panel discussion on sustainable fashion happening Thursday evening. “Dress code is creative business casual,” she adds, which could mean literally anything from “jeans without holes” to “avant-garde but make it office.” I look down at my current outfit—sweatpants with a coffee stain and a faded band t-shirt from 2007—and realize nothing in my clean clothes pile is going to cut it.

This is how I find myself power-walking through H&M on my lunch break, a man on a mission with exactly 47 minutes before I need to be back at my desk for a call. H&M—the Swedish fast fashion giant that somehow manages to be simultaneously too trendy for normal life and not quite trendy enough for fashion people. The place where sizing seems to have been determined by throwing darts at a numerical board while blindfolded.

I grab an armful of items in what I think is my size and head to the fitting room, where I’m about to relearn a lesson I’ve somehow forgotten since my last emergency H&M visit: their clothes are not designed for bodies that eat regular meals and occasionally exercise in ways that build certain muscle groups.

The first pair of trousers—allegedly my size according to the label—won’t even clear my thighs. The second pair goes on but creates a waistband situation reminiscent of a busted can of refrigerator biscuits. The third pair fits my waist perfectly but apparently assumes I have the legs of a daddy longlegs spider. I emerge from the fitting room 20 minutes later with exactly one item that fits—a plain black t-shirt that I could have bought literally anywhere.

This experience isn’t unique to me. I’ve watched friends of all genders, sizes, and body types struggle through the bizarre dimensional portal that is H&M’s sizing system. My buddy Marcus, who has the build of a former college athlete now enjoying regular happy hours, describes shopping there as “psychological warfare.” My friend Sarah, who wears standard sizes in most stores, recently held up a pair of H&M jeans and asked, “Is this meant for an adult woman or a particularly stylish toddler?”

So what actually fits at H&M when you have a human body rather than the apparently preferred dimensions of a praying mantis? After years of trial and mostly error—plus some extremely candid conversations with store employees who shall remain anonymous for their job security—I’ve compiled a field guide for navigating this treacherous retail terrain.

First, let’s address the elephant in the room: vanity sizing does not exist at H&M. While most American retailers have gradually increased their dimensions while keeping the same size number (making consumers feel better about themselves), H&M has stubbornly maintained European sizing standards that tend to run smaller than what Americans are used to. This means that if you typically wear a medium, you’re probably a large or XL at H&M. If you typically wear an XL, you might need to size up to their XXL or even look for items from their plus-size collection.

I learned this lesson the hard way after insisting I was a medium for years despite substantial evidence to the contrary. There’s something uniquely humbling about being unable to get your arms through the sleeves of a shirt in your “normal” size. Now I automatically grab at least one size up from my usual and save myself the existential crisis.

But here’s where it gets truly weird—the sizing isn’t even consistent within the store itself. H&M operates multiple lines under one roof, each with its own distinct fit profile. Their basic collection tends to run the smallest. The Divided collection (aimed at younger shoppers) is slightly more forgiving but cut for people who have never experienced the joy of proper Italian pasta. The Premium collection sometimes—sometimes—acknowledges that humans have three dimensions rather than two.

All of this is further complicated by H&M’s tendency to use different materials and cuts from season to season, even for seemingly identical items. The perfect t-shirt you found last summer will be replaced by this summer’s “same” t-shirt that is somehow two inches narrower in the shoulders and made of material with the stretch properties of cement.

“We regularly update our fits based on current trends,” an H&M corporate rep told me when I asked about this phenomenon for a previous article. Which is retail-speak for “we’ll make the arms skinnier whenever we feel like it, good luck keeping up.”

So what items actually work for regular human bodies? After conducting highly unscientific research (meaning I’ve wasted countless lunch breaks in their fitting rooms and interrogated everyone I know who shops there), I’ve identified some patterns.

For men with athletic builds (meaning you occasionally lift something heavier than a smartphone), the regular fit shirts are your best bet. Size up—always size up—and look for items with at least some stretch in the material. The slim fit shirts are designed for people shaped like pipe cleaners, no matter what size you choose. Their “muscle fit” should be renamed “compression garment” and approached with extreme caution unless you enjoy feeling like you’re wearing a sausage casing.

Blazers are actually a surprising win for many body types, especially the unstructured ones from their premium lines. They tend to have more generous cuts through the chest and shoulders than their other items, though the sleeves often run short. If you have longer arms, be prepared to wear them with the sleeves pushed up casually or budget for alterations.

Men’s pants present the greatest challenge for anyone with developed leg muscles. The “slim fit” can barely accommodate a normal human thigh, while the “skinny fit” seems designed for people who skip leg day for their entire lives. Your best options are either their straight fit or relaxed fit trousers, which actually accommodate things like quadriceps and calves. Their “regular fit” jeans are similarly forgiving, though they’ve been gradually slimming these down too in recent years.

For women, H&M’s sizing creates even more confusion thanks to their numerical system that corresponds to neither American nor traditional European sizing in any logical way. I’ve watched my friend Claire, who wears a consistent size 8 in most American brands, try on H&M items ranging from size 8 (too small) to size 14 (too big) in a single shopping trip.

“Their size 12 literally fits exactly the same as my size 8 jeans from Levi’s,” she told me while stress-eating a pretzel in the mall food court afterward. “Make it make sense.”

Women’s tops tend to be more forgiving than bottoms, with blouses and sweaters from the main collection generally accommodating a range of figures as long as you size up. Their basic t-shirts and tanks run notoriously small through the bust and shoulders, however, often requiring going up two sizes for a comfortable fit.

The dresses fall into two categories: shapeless sacks that look good on absolutely everyone, and structured sheaths that look good on approximately three people worldwide. There is no in-between. The wrap dresses are generally the most accommodating for different body types, while anything with a defined waist should be approached with caution and a willingness to try on multiple sizes.

Perhaps the most maddening aspect of H&M’s sizing isn’t just that it runs small—it’s that it’s wildly inconsistent. I’ve personally witnessed the same numerical size vary by what appears to be inches between different styles and collections. This isn’t unique to H&M—most fast fashion brands exhibit similar inconsistencies due to their distributed manufacturing and rapid turnover—but H&M seems to embrace this chaos with particular enthusiasm.

“I literally have to try on every single thing,” my friend Dana explained while showing me her H&M collection—a random assortment of sizes from XS to XL, all of which fit her perfectly. “The size is just a starting suggestion, not actual information.”

This inconsistency extends to H&M’s online shopping experience, which feels like playing a particularly frustrating lottery. The same item that fits perfectly in-store might arrive in a completely different dimension when ordered online, despite being labeled as the same size. This has led to my personal rule of never ordering anything from H&M that I haven’t already tried on in person—a policy that defeats the entire purpose of online shopping.

Mark, a fit model who occasionally works with mainstream retailers, offered some insight into why H&M’s sizing feels so disconnected from reality. “Most fast fashion brands aren’t fitting their clothes on a range of real bodies,” he explained. “They’re designing digitally and then maybe checking the sample on one or two fit models who are selected specifically because they have proportions that match the brand’s aesthetic ideal.”

What he’s diplomatically saying is that H&M, like many fashion brands, designs for the body they want you to have, not the body you actually do have. The difference is that higher-end brands usually account for this with more generous cuts, while H&M seems to have embraced aspirational sizing as a core philosophy.

Despite all these challenges, there are some genuine finds to be had at H&M if you know where to look and embrace a trial-and-error approach. Their knitwear tends to be more forgiving than their woven items. Anything with elastane or other stretch materials will accommodate a wider range of bodies. Oversized and boxy cuts—when you can find them—often work better for athletic or curvy figures than their standard fits.

The best strategy I’ve found is to completely ignore the size on the label and just grab multiple options of anything that catches your eye. I now routinely take the same item in three different sizes into the fitting room, treating the size label as more of a vague suggestion than actual information. It’s time-consuming and occasionally demoralizing, but it’s the only way to navigate a sizing system that seems designed by someone who’s never met an actual human being.

What makes this all the more frustrating is that H&M produces some genuinely good designs at accessible price points. Their collaborations with high-end designers bring interesting silhouettes to the masses. Their sustainable collections use innovative materials that are better for the planet. Their basic items can be the backbone of a versatile wardrobe—if you can find them in a size that acknowledges the existence of your ribcage.

I eventually found a decent outfit for that panel discussion, by the way. Black jeans (two sizes up from my usual), a simple oxford shirt (one size up, still tight in the shoulders), and an unstructured blazer that somehow fit perfectly off the rack, a miracle I’m still not entirely convinced wasn’t a hallucination induced by fitting room fluorescent lighting.

As I was checking out, the cashier looked at my selections and said, “Did you check the sizes? People usually need to size up here.” When I told her I already had, she nodded knowingly. “Smart. I work here and I still get it wrong half the time.”

That’s perhaps the most honest assessment of H&M sizing I’ve ever heard. Even the people who work there daily can’t consistently predict what will fit.

So the next time you find yourself in an H&M fitting room wondering if you’ve somehow grown three inches across the shoulders since breakfast, remember: it’s not you, it’s them. Their sizing exists in some parallel dimension where humans evolved differently—narrower, longer, and apparently without the need to ever raise their arms above shoulder height given how many of their shirts seem to restrict that particular movement.

Shop accordingly, bring your patience, and maybe eat before you go. Nothing makes weird sizing more traumatic than low blood sugar and fluorescent lighting. Trust me on this one.

The moment I knew men’s sizing had completely jumped the shark was during a particularly painful shopping trip with my friend Tony. Former college swimmer, still hits the gym five days a week, has the classic V-shaped torso that most guys would kill for. We were at a mid-range department store, and he was trying to find dress shirts for a new job.

“This one says ‘athletic fit,’” I pointed out, handing him what seemed like an obvious choice.

Tony disappeared into the fitting room, only to emerge looking like he was wearing a sail fashioned into a shirt. The shoulders drooped three inches past his actual shoulders. The waist could have fit another half-person inside it.

“What the hell?” he muttered, checking the tag again. “This is athletic fit?”

Two hours and seven stores later, we finally found shirts that fit him properly. They were labeled “slim fit.” Not athletic fit. Not regular fit. Certainly not “classic” or “traditional” fit, which made him look like he was a kid playing dress-up in his dad’s closet. The only shirts that actually accommodated his broader shoulders while tapering appropriately at the waist carried the “slim” designation.

That experience sent me down a rabbit hole of investigating what these ubiquitous yet wildly inconsistent fit labels actually mean across different American brands. The results were both fascinating and maddening—a hodgepodge of marketing terminology, arbitrary measurements, and competing definitions that make shopping unnecessarily complicated for men of all body types.

Let’s start with the basics. Most major American retailers and brands now offer multiple fits in their core categories (shirts, pants, suits, etc.). The exact terminology varies by brand, but you’ll commonly see labels like:

Regular/Standard Fit
Classic/Traditional Fit
Relaxed Fit
Slim/Tailored Fit
Athletic/Active Fit
Modern Fit

The problem? There is zero standardization across the industry about what these terms actually mean. One brand’s “slim” is another’s “regular.” One company’s “athletic” is looser than another’s “classic.” It’s a sizing Tower of Babel that leaves men frustrated, returns rates sky-high, and closets filled with clothes that never quite work.

“There’s no governing body that standardizes these terms,” explained Marcus, a technical designer I interviewed who’s worked for several major American menswear brands. “Each company defines them internally based on their target customer, their existing blocks [basic patterns], and frankly, marketing considerations.”

Those marketing considerations are crucial to understanding the chaos. As certain body types and silhouettes go in and out of fashion, brands adjust their terminology to seem current without necessarily changing their actual patterns significantly.

“Ten years ago, everyone wanted to offer ‘slim fit’ options because that was the trend,” Marcus continued. “But many mainstream brands didn’t actually make their slim fits particularly slim—they just needed the label to compete. Now ‘athletic fit’ is trendy terminology, but there’s even less consensus about what that actually means in practice.”

To make sense of this mess, I conducted a rather unscientific but revealing experiment. I measured identical size 40R suit jackets labeled as “athletic fit” from six different mainstream American brands. The variation was shocking:

Brand A’s athletic fit had a chest-to-waist drop (the difference between chest and waist measurements) of 8 inches.
Brand B’s was 6 inches.
Brand C’s was a mere 4 inches—actually less than their regular fit.
Brand D’s had a generous 10-inch drop but with narrower shoulders than their regular fit.
Brand E used the term for a jacket with a 7-inch drop but cut with extra material across the upper back.
Brand F’s athletic fit was identical to their regular fit but with slightly longer sleeves.

This is madness. How can the same term mean six completely different things?

The confusion extends to every category and body type. My friend Patrick, who has a more slender build, found that “slim fit” shirts from three different mall brands all fit him completely differently—one perfect, one still billowing at the waist, and one so tight he could barely move his arms.

“I’ve given up on the labels entirely,” he told me. “I just try everything on now, regardless of what it’s called.”

That’s wise advice, but it defeats the purpose of fit categorization, which supposedly exists to help streamline the shopping process. The whole point of these designations should be to guide customers toward products more likely to fit their particular body type. Instead, they’ve become essentially meaningless marketing terms.

So what’s actually going on with these labels, and how can men navigate them more successfully? After interviewing industry insiders and analyzing dozens of brands, I’ve identified some patterns in the madness:

“Regular” or “Standard” fit typically represents what the brand considers its core customer’s body type. For older, more established American brands (think Brooks Brothers, Lands’ End, L.L.Bean), this often means a boxier cut with ample room throughout. For newer brands targeting younger customers (J.Crew, Bonobos), “regular” typically has a more moderate silhouette. This is why a 40-year-old man who’s worn the same brands for decades might suddenly find “regular” fits too snug if he switches to a more contemporary brand.

“Classic” or “Traditional” fit is usually the roomiest option, designed with minimal tapering and maximum comfort in mind. But here’s where it gets tricky—some heritage brands use “classic” to describe their standard block, while others use it to denote their most generous fit. At Brooks Brothers, for instance, “classic” is roomier than “regular,” while at Ralph Lauren, the terms are sometimes used interchangeably.

“Slim” fit ostensibly offers a more tapered silhouette, particularly at the waist, with narrower cuts throughout. The degree of actual slimness varies dramatically by brand and target demographic. Gap’s slim fit, for example, is considerably more generous than J.Crew’s, which is itself less extreme than Zara’s. The age of the brand’s core customer is often the determining factor—the older the target demographic, the less actually “slim” their slim fit tends to be.

“Athletic” fit is the newest and most inconsistently applied term. In theory, it should accommodate broader shoulders and chests while tapering more significantly at the waist—designed for V-shaped torsos rather than straight or rounded ones. In practice, it means wildly different things across the industry. Some brands use it to describe what is essentially a slim fit with slightly more room in the chest and shoulders. Others use it for what amounts to a regular fit with marginally more tapering at the waist. Still others seem to use it interchangeably with “relaxed fit,” creating maximum confusion.

“Modern” fit is perhaps the most meaningless term of all—essentially a marketing catch-all that can mean anything from “less boxy than our traditional line” to “slimmer than regular but not as slim as slim.” It’s frequently employed when brands are trying to update their image without alienating existing customers.

The inconsistency creates genuine problems for men trying to build functional wardrobes. My friend Mike, who has the increasingly common body type sometimes called “skinny-fat” (slim limbs but carrying weight around the middle), finds himself in a particular sizing purgatory.

“Slim fits work for my arms and legs but not my midsection,” he explained during a frustrated shopping trip. “Regular fits work for my waist but look sloppy everywhere else. And athletic fits assume I have this broad chest and shoulders that I don’t have. I basically can’t win.”

For men with more muscular builds, the situation can be equally frustrating. Despite the proliferation of “athletic fit” options, many are athletic in name only. Derek, a personal trainer with the classic gym-built physique (broader shoulders, developed chest, narrower waist), has to size up in most shirts to fit his shoulders and chest, then get the waist taken in by a tailor.

“It’s like they think ‘athletic’ just means ‘slightly less fat,’” he observed after trying on yet another disappointing “athletic fit” button-down. “They don’t actually design for guys who lift.”

So how can men navigate this confusing landscape more successfully? Some practical strategies I’ve developed after years of helping men shop:

Ignore the labels initially and focus on measurements. Many brands now provide detailed sizing information online, including actual measurements for each fit type. Pay attention to chest-to-waist drop for jackets and shirts, rise and thigh measurements for pants, and shoulder width for anything worn on the upper body. These numbers tell you far more than the fit names ever will.

Identify brands that actually design for your specific body type. Through trial and error, you’ll discover which companies consistently work for your particular proportions. For V-shaped torsos, Peter Manning and Bonobos often deliver on their athletic fit promises. For slender builds, Suit Supply and Uniqlo provide genuinely slim options. For larger guys, Duluth Trading and Eddie Bauer offer well-designed regular and relaxed fits.

Learn your alterations budget. Some fit issues can be easily and affordably addressed by a tailor (waist suppression, sleeve and trouser length), while others are prohibitively expensive or practically impossible (shoulder width, neck circumference, rise in pants). Shop for items that fit in the hard-to-alter areas, and budget for adjustments to the rest.

Try one size up and one size down from what you think you need, especially when shopping a brand for the first time. Vanity sizing runs rampant in menswear, meaning a 34″ waist rarely measures 34 actual inches, and the degree of discrepancy varies widely between brands.

Look beyond the mass market. Some of the most innovative fitting options now come from digitally-native brands like Peter Manning (for shorter men), American Tall (for taller guys), and Bonobos (with their multiple fit options in the same styles). These companies have built their business models around solving fit problems that traditional retailers have ignored.

A particularly promising development is the emergence of brands offering the same style in multiple fits. Bonobos pioneered this approach with their chinos available in slim, tailored, athletic, and straight fits, all with the same design details and color options. This model allows men to find their optimal fit without compromising on style preferences.

“We realized that body diversity is just as significant as style diversity,” explained Craig, a product developer at a major American menswear brand that recently expanded their fit options. “The old model of forcing different bodies to adapt to a single fit standard just doesn’t make sense anymore, especially when manufacturing technology makes multiple blocks relatively easy to implement.”

The most encouraging trend I’ve observed is increased transparency about actual measurements. Forward-thinking brands have begun providing comprehensive sizing information for each fit variation—not just basic chest/waist numbers but details like shoulder width, sleeve opening, thigh circumference, and rise measurements. This allows men to make informed decisions based on their actual bodies rather than ambiguous fit terminology.

Until the industry adopts standardized definitions (which, let’s be honest, is unlikely to happen anytime soon), our best defense as consumers is information and experience. Learn your key measurements, understand which dimensions are most problematic for your particular body type, and keep records of which brands and fits consistently work for you.

And perhaps most importantly, remember that fit issues rarely reflect a problem with your body—they’re a problem with the clothing. When my swimmer friend Tony couldn’t fit into shirts properly, the issue wasn’t his perfectly healthy, athletic physique; it was an industry using misleading labels and designing primarily for a limited range of body types.

The next time you’re standing in a fitting room wondering how a “slim fit” could possibly be hanging off you like a tent, or how an “athletic fit” seems to have been designed for someone with the proportions of SpongeBob SquarePants, take comfort in knowing you’re not alone. The system is confusing by design, not by accident.

But with a better understanding of what these labels actually mean (or don’t mean), you can approach shopping more strategically, waste less time and money on ill-fitting clothes, and eventually build a wardrobe of pieces that genuinely work for your unique body—whatever arbitrary fit category it might or might not fall into.

My first encounter with color analysis was in my mom’s dog-eared copy of “Color Me Beautiful” that lived on our bathroom shelf throughout my childhood. I distinctly remember the slightly creepy photos of women divided into seasons – each draped in color swatches that supposedly complemented their natural coloring. One summer afternoon when I was fourteen and spectacularly bored, I decided to figure out which “season” I was. After thirty minutes of pressing random fabric scraps from Mom’s sewing box against my face and squinting critically at my reflection, I determined I was either a “Winter” or possibly just really bad at this whole color theory thing.

Two decades later, I found myself in Milan during fashion week, having drinks with a legendary Italian menswear designer who shall remain nameless (though his scarves probably appear regularly in your Instagram feed). After several Negronis, I confessed my teenage color palette confusion. He roared with laughter, then leaned in conspiratorially: “The whole season system? Complete bullshit. Italian men have worn the same colors for centuries because they work. Navy, gray, burgundy, olive. These aren’t ‘Winter’ colors or ‘Summer’ colors. They’re just good colors.” He gestured dramatically toward a particularly well-dressed gentleman across the bar. “You think that man asked his tailor if he’s an Autumn? No! He knows what looks good. The rest is marketing.”

While I wouldn’t quite call the seasonal color system complete bullshit (sorry, Giuseppe), my journey through menswear has convinced me that traditional color analysis is, at best, an oversimplified starting point and, at worst, a limiting framework that ignores the complex reality of how color actually works on different people. The problem isn’t that colors don’t matter – they absolutely do – but rather that most color systems rely on crude categorizations that fail to capture the subtle interplay between your unique coloring and the clothes you wear.

I’ve spent years watching guys struggle with color choices. Tom, a design director friend with reddish hair, had been told by some color consultant that as a “Spring,” he should never wear black. He dutifully purged his wardrobe of anything remotely close to black and wondered why he suddenly looked washed out in the muddy beiges he’d been prescribed. There was Mike, who embraced his “Winter” diagnosis so enthusiastically that his closet transformed into a kaleidoscope of jewel tones that overwhelmed his otherwise fairly subdued personality. And countless others who simply gave up on the whole concept, retreating to the safety of navy and gray because figuring out their “best colors” seemed like deciphering ancient hieroglyphics.

The reality is both simpler and more complex than seasonal color systems suggest. Finding your personal color palette isn’t about fitting into predetermined categories; it’s about understanding a few fundamental principles and then observing, testing, and refining based on your unique characteristics. After helping hundreds of men navigate the confusing world of color, I’ve developed an approach that actually works without requiring you to memorize which season can wear mustard yellow (it’s Autumn, apparently, though I’ve seen plenty of “Winters” rock it just fine).

Let’s start with the principles that actually matter. The traditional seasonal system gets a few things right: your natural coloring – skin tone, hair color, and eye color – does create certain harmonies and dissonances with different colors. But rather than trying to categorize yourself, focus on understanding three key relationships: contrast levels, undertones, and color intensity.

Contrast is perhaps the most immediately observable element of your natural coloring. Take a clear, unfiltered photo of your face in natural daylight. How much difference is there between your skin tone, hair color, and eye color? Some guys have high natural contrast – think pale skin with dark hair and eyes, or deep skin with very light eyes. Others have low contrast – where hair, skin, and eyes are closer in value (lightness or darkness). Your most flattering outfits will generally echo your natural contrast level.

My friend David has extremely high contrast coloring – paper-white Irish skin and jet-black hair. When he wears similarly high-contrast combinations (crisp white shirt with black jacket, for instance), he looks put-together and harmonious. When he wears low-contrast outfits (beige with light blue, for example), he looks washed out and somehow unfinished. Meanwhile, my buddy Ryan has the classic low-contrast Scandinavian thing going on – light skin, blonde hair, blue-gray eyes. High-contrast outfits overwhelm his natural coloring, while tone-on-tone combinations enhance his features.

This contrast principle alone is more useful than most seasonal advice, but it gets even more interesting when you apply it to specific clothing choices. High-contrast guys can generally wear more dramatic color combinations – burgundy with white, navy with yellow, forest green with pink. Low-contrast guys tend to look better in more subtle pairings – olive with tan, navy with gray, burgundy with brown.

The second critical factor is undertone – the subtle hues beneath your surface skin color. Regardless of how light or dark your skin is, the underlying tone tends toward either warm (yellow/golden/peachy) or cool (pink/red/bluish). This undertone affects how colors look against your skin far more than whether you’re a “Summer” or “Winter.”

Determining your undertone can be tricky, but there are a few reliable indicators. Check the veins on the inside of your wrist – bluish veins typically suggest cool undertones, while veins appearing more green indicate warmer undertones. Another test: do you look better in pure white or off-white/ivory? Pure white typically flatters cool undertones, while warmer off-whites complement warm undertones. Gold versus silver jewelry provides another clue – most people intuitively gravitate toward the metal that harmonizes with their undertone.

Once you’ve identified your undertone, you can better understand why certain colors have always worked for you while others never quite looked right. Warm undertones usually harmonize with earthy colors (olive, camel, rust, burnt orange), while cool undertones typically pair better with jewel tones and clearer colors (royal blue, emerald, true red).

The final piece of the puzzle is color intensity – how saturated or muted your natural coloring appears. Some guys have naturally vibrant coloring – clear eyes, distinct hair color, skin with a noticeable glow. Others have more muted, softened coloring. Your most flattering colors will generally match this intensity level.

My editor Michael has that classic Italian coloring – olive skin, dark brown hair with rich undertones, and amber-brown eyes. When he wears similarly rich, slightly muted colors (burgundy, forest green, tobacco brown), he looks completely in harmony. Pastel colors make him look like he’s recovering from food poisoning. By contrast, my art director Chris has that classic Nordic thing happening – clear blue eyes, bright blonde hair, and fair skin with a distinct pink undertone. Vibrant, clear colors enhance his natural coloring, while the earthier tones that work so well for Michael make Chris look like he needs a multivitamin.

This is where most color systems go wrong – they try to categorize people into rigid groups rather than recognizing that we each exist on a spectrum of contrast, undertone, and intensity. The “season” you’re assigned might get one or two of these factors right while completely missing the others.

So how do you put this into practice? Start by forgetting everything you’ve been told about which “season” you are and observe your natural coloring objectively. Take photos in natural light and analyze your contrast level, undertone, and color intensity without trying to fit yourself into a predetermined box.

Then comes the fun part: experimentation. Instead of purchasing a whole new wardrobe based on some color consultant’s proclamations, use the changing room as your laboratory. Grab the same shirt in different colors and photograph yourself wearing each one in similar lighting. Don’t just ask “does this look good?” but rather “what is this color doing to my face?” Some colors will make your complexion look more even and your eyes brighter; others might emphasize tiredness or bring out unevenness you didn’t even know was there.

My own changing room experiments led to some surprising discoveries. Despite being told I was a “Winter” who should stick to cool, clear colors, I found that certain warm tones – particularly rich browns and burnt oranges – actually brought out warmth in my skin and made me look healthier. Meanwhile, the icy pastels I was supposedly born to wear made me look like I needed immediate medical attention. Had I rigidly followed the season system, I’d have missed out on some of my most flattering colors.

This experimental approach has worked for countless guys I’ve advised. Take Ryan, a finance guy who’d been told by a style consultant that as a “Spring” he should avoid black at all costs. After our session experimenting with different combinations, he discovered that while head-to-toe black wasn’t his best look, a black knit with dark jeans actually emphasized the blue in his eyes and created a sophisticated frame for his face. The seasonal system’s blanket prohibition had been holding him back.

As your color confidence grows, you’ll start noticing patterns and developing reliable instincts. Colors that consistently earn you compliments or make you feel particularly good are giving you valuable data. Pay attention to these patterns – they’re often more telling than any color analysis chart.

It’s also worth considering the contexts in which you wear certain colors. Some of my theoretically “worst” colors actually photograph incredibly well for work purposes. While mustard yellow supposedly clashes with my “Winter” coloring, I’ve found it reads beautifully on camera and creates a distinctive look that’s become something of a signature. Context matters.

Perhaps the most liberating realization is that your “perfect” colors aren’t a life sentence. As we age, our natural coloring changes – hair grays or recedes, skin tone shifts subtly, even eye color can appear different with time. The colors that flattered you at 25 might not be your best choices at 45. Treating color as an ongoing experiment rather than a rigid system allows you to evolve your palette naturally.

Then there’s the simple fact that personal style sometimes trumps theoretical flattery. One of the most stylish men I know consistently wears colors that, according to traditional analysis, should be terrible with his coloring. But his confidence and the thoughtful way he combines these supposedly unflattering shades create a compelling and distinctive presence. The “rules” are ultimately just suggestions.

If you take nothing else from this rambling color manifesto, remember this: no color chart, season designation, or style consultant knows better than your own mirror and camera. The colors that make you look alive, that emphasize your best features, and that make you feel confident are your colors – regardless of what category they supposedly belong to.

Giuseppe was onto something with his Negroni-fueled color theory dismissal. Those classic menswear colors – navy, gray, olive, burgundy – have stood the test of time not because they flatter one specific “season,” but because they’re inherently versatile and generally harmonize with a wide range of natural coloring. If you’re completely overwhelmed by color choices, starting with these tried-and-true options is never a bad move.

But for those ready to move beyond the basics, liberating yourself from oversimplified seasonal designations opens up a world of possibilities. Your personal color palette isn’t something to be discovered through a quiz or prescribed by a consultant – it’s something you develop through observation, experimentation, and an honest assessment of what actually works for you, not what supposedly should work based on which arbitrary season you’ve been assigned.

Now if you’ll excuse me, I need to go put on my supposedly unflattering burnt orange sweater. It might break the “Winter” rules, but damn if it doesn’t make my eyes pop.

I killed a t-shirt last week. Not like, “oh this doesn’t fit right anymore” killed it. I mean I put it on, raised my arms to grab a coffee mug from the cabinet, and the entire right seam split open like I was auditioning for an off-Broadway production of The Incredible Hulk. The shirt was from one of those fast fashion retailers I won’t name (but rhymes with “shmeverlane”), cost about $15, and had survived exactly seven wears and three washes.

Standing in my kitchen, now essentially wearing half a shirt and feeling the cold air on my exposed ribs, I had to reckon with an uncomfortable truth: I, a supposed menswear expert who literally gets paid to have opinions about clothes, had been suckered by the siren song of cheap, trendy crap. Again.

And look, I get it. The temptation is real. When you can get an entire outfit—shirt, pants, even a jacket—for less than what a quality pair of shoes would cost, the math seems simple. Especially when these clothes often look pretty damn good… at first. They’re designed to hit that initial dopamine rush of “new clothes feeling” without any consideration for what happens three washes later.

This pattern used to define my early twenties. I’d blow my meager editorial assistant paycheck on whatever trendy items I saw in the windows along Broadway, wear them a handful of times, and then watch them disintegrate, pill, fade, or warp into unwearable shapes within months. It was a cycle that felt affordable in the moment but added up to thousands of dollars literally thrown in the trash.

The wake-up call came when I was helping my mom clean out my childhood bedroom and found a J.Crew oxford shirt my dad had handed down to me in high school. Ten years and countless washes later, it looked better than stuff I’d bought six months earlier. The fabric had softened beautifully, the collar still stood properly, the buttons were all intact. Meanwhile, the “premium” fast fashion button-down I was currently wearing already had a weird bacon-collar situation happening after just a few months.

That’s when it clicked: I wasn’t saving money with cheap clothes. I was wasting it.

But here’s the thing—the alternative doesn’t have to be dropping $400 on a shirt or only shopping at luxury boutiques that offer you sparkling water while you browse. There’s this sweet spot of brands and items that cost just a bit more than fast fashion but deliver exponentially better value. These are the clothes that, amortized over their actual lifespan, end up being cheaper per wear than almost anything else in your closet.

Take t-shirts, for instance. I used to buy packs of them for $10-15 each, replacing them every few months as they twisted into weird crop tops after washing. Then a stylist friend introduced me to a small American manufacturer making tees for $30. “Thirty bucks for a plain t-shirt? Are you high?” was my initial reaction. But these shirts are still in my rotation four years later. The math is clear: six cheap $15 shirts replaced twice a year for three years = $180. Three good $30 shirts that last three years = $90.

This principle applies across basically every category of menswear. Everlane’s $68 chinos might seem steep compared to H&M’s $25 version, but when the H&M pair bags out at the knees and fades unevenly after a month while the Everlane pair stays sharp for a year, you’re actually spending more on the “budget” option.

My friend Trevor—yes, the one whose dad works for Hugo Boss, he’s still insufferably well-dressed—calls this the “fake broke tax.” It’s the premium you pay for thinking you’re saving money when you’re actually spending more in the long run. And the worst part? You don’t even look good while paying it.

So where are these magical middle-ground brands that offer the best quality-to-price ratio? I’ve spent years finding them through trial, error, and more blown-out seams than I care to admit. Here’s what I’ve discovered:

For basics like t-shirts, underwear, and socks, brands like Uniqlo’s Supima cotton line, Asket, and Kotn offer quality that rivals luxury brands at prices just slightly above fast fashion. The $15 vs. $30 t-shirt example isn’t theoretical—that’s the actual price difference, and the longevity difference is real.

When it comes to denim, the sweet spot is usually between $80-150. Brands like Naked & Famous, Nudie Jeans, and even Levi’s Made & Crafted line occupy this territory. The jump in quality from a $40 pair to a $100 pair is massive, while the difference between a $100 pair and a $300 designer pair is often minimal for anyone who isn’t a denim obsessive.

For button-up shirts, I’ve found brands like Spier & Mackay, Charles Tyrwhitt (when on sale), and even J.Crew (again, on sale—never pay full price there) offer substantial quality around the $70 mark. These shirts will last years rather than months.

Footwear is where this principle becomes most obvious. The gap between a $100 shoe and a $200-300 shoe is the difference between replacing them annually and resoling them after five years. Brands like Meermin, Thursday Boots, and Grant Stone occupy this middle territory where the construction quality takes a quantum leap without the price doing the same.

The trick is recognizing when spending more actually gets you better quality versus when you’re just paying for marketing or designer prestige. Some guidelines I’ve developed:

Check the fabric weight. Heavier doesn’t always mean better, but substantial fabric is generally a good sign, especially for items like shirts and pants. If something feels flimsy in your hands, it will look flimsy on your body.

Examine the stitching. More stitches per inch generally indicates better construction. Reinforcement at stress points is crucial—that’s actually what failed on my split t-shirt.

Look at seam finishing. Raw, unfinished seams are a red flag at any price point. Clean, flat seams that don’t twist or bunch are worth paying extra for.

Research construction techniques. Welted shoes can be resoled, extending their life indefinitely. Jeans with selvedge outseams tend to hold up better to repeated washing. Shirts with pattern matching at the seams indicate attention to detail that correlates with overall quality.

I’m not suggesting you need to become a textile engineer or spend hours researching every purchase. But developing a basic understanding of quality markers will save you thousands over time. And honestly? It’s kind of fun to become the guy who can spot good construction at thirty paces. My friends now send me photos from dressing rooms asking for quality checks, and I feel like some kind of clothing psychic telling them, “Those seams will fail within a month” (I’m usually right).

The other approach is to simply look at brands operating in that middle territory where they’re focused on materials and construction rather than trend-chasing or logo placement. Some consistently reliable options include:

Taylor Stitch, whose $125 shirts and $150 pants are built like tanks but look refined.
Buck Mason, with basics that cost maybe 30% more than Gap but last 300% longer.
Universal Works, offering workwear-inspired pieces with excellent fabric sourcing.
Portuguese Flannel, making shirts that rival ones three times their price.
Reigning Champ for sweatshirts and casual wear that actually gets better with age.

These aren’t exactly budget brands, but they’re accessible splurges that pay dividends. Save up for one good piece instead of three disposable ones.

Another strategy? Be patient and shop the sales. That $150 jacket might hit $75 at end-of-season, at which point it’s competing with fast fashion prices while offering substantially better quality. I’ve built probably 60% of my wardrobe this way—buying better brands at deep discounts rather than cheaper brands at full price.

The most sustainable clothes—both environmentally and financially—are the ones you don’t replace. My closet now contains fewer items than it did five years ago, but they’re better made, more versatile, and ironically cost me less annually because they don’t need constant replacement.

That doesn’t mean I never buy from fast fashion retailers—I’m not made of money, and sometimes you need something specific for a one-time event. But I’ve learned to be strategic about it. If it’s a core piece I’ll wear regularly, I spend more upfront. If it’s a super-trendy item that might look dated in six months, maybe that’s where I’ll go cheaper (though vintage/secondhand is often even better for trend experimentation).

The final piece of this puzzle is care. Even well-made clothes will fail if treated poorly. Washing cold, hanging to dry when possible, folding knits instead of hanging them, using shoe trees—these habits extend the life of everything in your wardrobe, making even moderately priced items perform like luxury ones.

My split-seam t-shirt incident became a moment of reckoning. I gathered all the fast fashion in my closet, assessed what was already showing signs of wear, and made a plan to gradually replace those items with better versions as they fail. It’s not about overnight transformation—it’s about shifting your default settings over time.

Last month, I splurged on a $68 waffle henley from a small American manufacturer that specializes in heavyweight knits. It replaced a similar $25 version that had already started unraveling at the cuffs after just four wears. When I mentioned the price to my dad on our weekly call, he did his usual “you paid WHAT for a shirt?” routine. I just smiled and told him to ask me again in five years when I’m still wearing it.

The cheap shirt is gone. That money is gone too. The slightly more expensive, significantly better shirt will be with me for years. In the long game of looking good while managing money, that’s what victory looks like.

I’ve got a pair of black cap-toe oxfords sitting on my desk as I write this. The left shoe cost $59.99 at a department store sale. The right shoe cost $495 from a reputable English shoemaker. From three feet away, they look nearly identical. Both are black. Both have cap toes. Both have that essential dress shoe silhouette. My editor walked in, glanced at them, and asked why I had two of the same shoe on display. But these shoes – seemingly similar at a casual glance – represent two entirely different approaches to footwear, with material and construction differences that go far beyond marketing hype or brand prestige.

The great men’s dress shoe debate might be the most confusing cost-to-value proposition in menswear. We’ve all heard the various arguments: “Expensive shoes last longer, so they’re actually cheaper over time” or the counterpoint, “Modern manufacturing has made those price differences obsolete.” But which is true? Is there really a meaningful difference between shoes at different price points, or are we just paying for brand names and marginally better aesthetics?

After fifteen years covering menswear and personally wearing everything from $40 Payless disasters to embarrassingly expensive hand-welted masterpieces, I’ve developed a nuanced understanding of the real differences across price tiers. And since I’ve got no skin in the game – I don’t own stock in Allen Edmonds or get kickbacks from Meermin – I can offer an objective breakdown of what you’re actually getting (or not getting) as you climb the dress shoe price ladder.

Let’s start with the most obvious difference between my $60 department store oxford and its $500 counterpart: materials. The budget shoe is made from what the industry euphemistically calls “genuine leather,” which sounds impressive but is actually one of the lowest grades of leather available. It’s essentially the leftover material after higher-quality sections have been claimed for premium products. This leather has typically been heavily corrected (sanded to remove imperfections) and then coated with a plastic-like finish to create a uniform appearance.

The $500 shoe, by contrast, is made from full-grain calfskin – the highest quality and most durable leather available for footwear. Full-grain leather retains the natural grain and imperfections of the hide, developing a unique patina over time rather than wearing out. The difference becomes immediately apparent with use – the cheap leather will crease sharply and often crack along those creases, while quality full-grain leather develops subtle, rolling creases that add character without compromising structural integrity.

This material difference extends to the soles as well. My budget oxford has a synthetic rubber sole designed to imitate leather. It’s glued (not stitched) to the upper and will typically wear through within a year of regular use. Once that happens, the shoe is essentially garbage – the cost of replacing a glued sole, if a cobbler will even attempt it, often exceeds the original price of the shoe.

The $500 shoe features a oak-bark tanned leather sole that’s Goodyear welted to the upper – meaning it’s attached via a sophisticated stitching method that allows for repeated resoling as it wears down. This construction essentially makes the shoe rebuilable multiple times, extending its potential lifespan from months to decades. My cobbler in Brooklyn has clients still wearing the same premium dress shoes they purchased in the 1980s, thanks to periodic resoling and care.

The interior components reveal even more dramatic differences. Budget dress shoes typically use fiberboard or other synthetic materials for structural elements like the insole and heel counter. These materials initially provide adequate structure but quickly break down with wear and moisture exposure. Ever had a dress shoe that suddenly seemed to collapse or lose its shape after a few months? That’s likely because the cardboard-like structural components gave up the ghost.

Premium shoes use leather for virtually all internal components – vegetable-tanned leather insoles that mold to your foot over time, leather heel counters that maintain their shape for years, and often leather linings rather than synthetic fabrics. This all-leather construction not only lasts longer but also provides superior comfort as the shoe breaks in, conforming to your unique foot shape rather than breaking down.

The construction methods employed represent perhaps the most significant functional difference between price tiers. My $60 oxford is made using what’s called cement construction – essentially, the upper is glued to the sole using strong adhesives. This method is fast, inexpensive, and requires minimal skilled labor, making it perfect for mass production. The downside? Once that glue bond fails (and it eventually will), the shoe is effectively dead.

The $500 shoe uses Goodyear welt construction, a complex method where a strip of leather (the welt) is stitched first to the upper and insole, then to the outsole. This creates a sort of leather sandwich with the upper trapped securely between layers, all held together with heavy-duty stitching rather than glue. The result is a shoe that can be resoled multiple times by simply removing the stitching, replacing the worn sole, and restitching – all without damaging the upper. Some premium shoes use even more labor-intensive methods like hand-welting or Norwegian construction, which can push prices well beyond the $500 mark.

These construction differences directly impact not just longevity but also comfort and performance. Cheaply constructed shoes rely heavily on padding and cushioning to provide initial comfort, since the structural elements don’t conform to your foot. Like a mattress that feels great in the showroom but develops body-shaped depressions after six months, this approach feels good initially but deteriorates quickly.

Quality welted shoes often feel relatively stiff at first but gradually conform to your foot’s unique shape, creating a custom-fit feel that actually improves with wear. The leather insole develops indentations that match your foot perfectly, while the cork filling often found beneath the insole in welted shoes compresses to create custom arch support. This break-in process requires patience but results in shoes that can be worn comfortably for 12+ hour days once properly conformed to your feet.

The aesthetic details and finishing touches also separate price tiers, though these differences are more about craftsmanship pride than functional benefits. My budget oxford has machine-finished edges that are uniformly perfect but somewhat plasticky in appearance. The stitching is mechanically precise but lacks character, and the overall silhouette is acceptable but not particularly elegant. It was designed to hit a price point first and foremost.

The $500 shoe shows hand-burnished toe caps with subtle color variation, meticulously finished sole edges with multiple layers of dye and wax, and hand-detailed brogueing where applicable. The leather has been skillfully shaped around a last (the foot-shaped form used in shoemaking) designed for aesthetic elegance rather than merely production efficiency. The result is a shoe with visual depth and character that actually looks better as it ages rather than simply wearing out.

But let’s be honest about the elephant in the room: diminishing returns. The quality improvement from a $60 shoe to a $250-300 shoe is dramatic and objectively worthwhile for anyone who wears dress shoes regularly. The jump from $300 to $500 is noticeable but less revolutionary. Beyond $500, you’re often paying for increasingly subtle refinements, heritage brand prestige, or hand-made exclusivity rather than proportional quality improvements.

This creates several sweet spots depending on your needs and budget. For occasional dress shoe wearers – the wedding/funeral/job interview crowd – spending more than $150-200 probably doesn’t make practical sense. You’ll get a decent-looking shoe that will survive its limited use cases before style changes or growing feet necessitate replacement anyway.

For regular dress shoe wearers, particularly those in conservative professional environments, the $300-400 range from makers like Allen Edmonds, Meermin, or Grant Stone offers perhaps the optimal value proposition. These shoes feature full-grain leather, Goodyear welt construction, and respectable aesthetics without the heritage markup of European luxury brands.

For those seeking the best long-term investment or appreciating the finer subtleties of traditional shoemaking, established brands in the $500-700 range like Alden, Crockett & Jones, or Carmina offer a balance of quality and prestige without venturing into the truly exclusive stratosphere of bespoke or ultra-luxury options.

My personal collection reflects this analytical approach. After years of trial, error, and more than a few painful blisters, I’ve settled on a core rotation of mid-to-high-end welted shoes for daily professional wear, supplemented with a few strategic budget options for specific situations – like keeping a pair of decent-looking cheap oxfords in my desk drawer for unexpected client meetings when I’ve worn sneakers to the office.

The long-term economics are fascinating as well. That $60 department store oxford will typically last about one year of regular rotation before looking so degraded that replacement becomes necessary. The $500 welted shoe, with proper care and periodic resoling (about $80-100 every two years for someone wearing them 2-3 times weekly), can easily last 10+ years. Over a decade, you might spend $600 on the quality shoe ($500 initial + one resoling) versus $600 on replacing the cheap shoe annually – for identical total cost but dramatically different day-to-day experience and environmental impact.

Of course, this perfect economic equilibrium assumes you don’t change shoe size, the style remains relevant, and you maintain consistent use patterns. Life is rarely so predictable. Many guys find their feet change subtly as they age, or their professional environment shifts to more casual standards, making those decade-long projections somewhat theoretical. This is where more moderate options in the $200-300 range may actually represent the most practical sweet spot for many.

What about the middle ground – those $100-200 dress shoes that dominate department store selections? This price tier often represents the worst value proposition, featuring marginally better materials than budget options but rarely the fundamental construction quality that enables long-term use. These shoes typically employ slightly better leathers or aesthetic details while still using glued construction that dooms them to a similar lifespan as their cheaper counterparts.

There are exceptions worth noting. Some brands have managed to deliver welted construction at surprisingly accessible price points by leveraging overseas production while maintaining quality standards. Meermin starts around $200 for Goodyear welted shoes, while Beckett Simonon offers blake-stitched options (another resoleable construction method) in the same range through their direct-to-consumer model. These represent genuine value outliers in an otherwise predictable price-to-quality correlation.

The used market presents another fascinating value proposition. Quality welted shoes can be refurbished remarkably well, making second-hand Allen Edmonds or Aldens (often available for $150-200) potentially better values than new shoes at similar prices. This approach requires patience and a willingness to gamble occasionally, but it’s how I built my initial quality shoe rotation as a broke assistant editor a decade ago.

When assessing dress shoes across price tiers, I encourage guys to consider three separate factors: appearance, comfort, and longevity. Budget shoes often nail the first criteria initially – they can look perfectly acceptable out of the box. They typically fail on the second two metrics, becoming uncomfortable quickly and deteriorating visibly within months. The true measure of quality footwear is how it performs a year into ownership, not how it looks in the store display.

The real luxury of quality shoes isn’t the brand name or the prestige – it’s never having to think about your shoes during a long day. It’s the confidence of knowing your footwear won’t let you down aesthetically or functionally, even after hours of wear. That peace of mind has genuine value beyond material or construction specifications, especially for those who rely on professional presentation as part of their livelihood.

So what’s the verdict on that $60/$500 pair staring at me from my desk? The expensive shoe is objectively, meaningfully better in almost every measurable way. It will last longer, age more beautifully, feel better after the break-in period, and maintain its shape and appearance through years of wear. But that doesn’t automatically make it the “right” choice for everyone.

The best dress shoe for you exists at the intersection of your actual wearing habits, realistic budget, and personal priorities. Someone wearing dress shoes five days a week in a formal business environment might find even $500 shoes a practical investment. Someone needing dress shoes twice a year for special occasions might find budget options completely adequate. The trick is honest self-assessment about your needs rather than succumbing to either false economy or aspirational overspending.

As for me, I’m heading to a wedding this weekend wearing welted oxfords I’ve owned for eight years, recently resoled for their third life cycle. They’ve molded perfectly to my feet, developed a rich patina, and cost me effectively $50 per year of ownership. But I keep that $60 pair in my closet too – because sometimes you just need shoes you don’t have to worry about at a backyard barbecue when an unexpected summer shower rolls in. In footwear as in life, context matters.

My dad’s closet was a fascinating horror show throughout my childhood. The man owned not one but three windbreakers in varying shades of teal and purple (it was the ’90s, but still). His collection of light-wash jeans would have made Jerry Seinfeld weep with joy. And the crown jewel of his weekend wardrobe was a pair of blindingly white New Balance 624s that he wore to mow the lawn, go to Home Depot, grill burgers, and pretty much everything else that didn’t involve his office job.

I remember swearing to myself at age 14, while watching him cheerfully pair those sneakers with calf-high white socks and cargo shorts, that I would rather literally die than dress like that when I grew up. The universe, it turns out, has a perverse sense of humor.

Last weekend, I found myself in a Manhattan vintage store trying on a mint-condition windbreaker in a shade that can only be described as “aggressive teal.” My girlfriend watched with a mixture of horror and amusement as I admired it in the mirror. “Isn’t that exactly like the jacket you used to make fun of your dad for wearing?” she asked. I paused, windbreaker half-zipped, confronted with the terrible truth: I had become everything I once mocked.

But here’s the thing—the jacket looked good. Not despite its dad-ness but somehow because of it. Paired with simple black jeans and minimalist sneakers rather than my father’s preferred pleated khakis and lawn-mowing shoes, it had transformed from embarrassing relic to fashion statement. I bought it immediately and have worn it three times since, receiving compliments each time.

The fashion industry’s endless cycle of irony and reappraisal has fully embraced what we once dismissed as “dad style.” The very aesthetic elements we ran from as teenagers—chunky sneakers, relaxed fits, practical outerwear, fanny packs (sorry, “belt bags”)—have been reclaimed, recontextualized, and frankly, improved. What was once the uniform of middle-aged suburban malaise is now the foundation of some of the most influential looks in contemporary menswear.

This isn’t just about fashion’s love of irony, though that’s certainly part of it. It’s also about a genuine reevaluation of what makes clothes good. The comfort and functionality that dads prioritized (while we were busy squeezing into skinny jeans that required lying down to zip up) actually make a lot of sense. Turns out the old guys might have been onto something with their roomy fits and practical pockets. They just needed some help with execution.

So let’s break down the dad trends worth reconsidering and how to wear them without looking like you’re actually headed to a neighborhood association meeting.

The dad shoe—specifically the chunky training sneaker—might be the most emblematic piece of this whole movement. What started with fashion insiders ironically embracing the aggressively normal New Balance 990s has evolved into a genuine appreciation for these supremely comfortable, deliberately unstylish kicks. The key difference between how they’re worn now versus how our dads wore them is all about context and proportion.

My neighbor Bob wears his gray New Balance 990s with relaxed-fit Dockers and tucked-in polos, creating a look that screams “I’m going to the hardware store.” When worn with cropped trousers, interesting socks, and a deliberately oversized sweatshirt or sharp jacket, those same shoes become a statement piece rather than a surrender to comfort. The contrast between the deliberately clunky footwear and more contemporary elements creates tension that reads as intentional rather than oblivious.

I resisted the dad shoe trend for years, clinging to my sleek minimal sneakers like they were the last vestige of youth. Then Trevor convinced me to try on a pair of 990v3s during a weekend shopping trip. The cloud-like comfort was immediately apparent, but what surprised me was catching my reflection and realizing they didn’t look half bad with my slim black jeans and unstructured blazer. They’ve since become my go-to travel shoes, carrying me through airport terminals with a comfort my Adidas Sambas never could. My father, when he noticed them during a recent visit, simply nodded and said, “Finally got sensible shoes, huh?” The satisfaction in his voice was unbearable.

Another dad staple experiencing a renaissance is the humble fleece. Once the uniform of nature documentary cameramen and suburban fathers at Saturday soccer games, the textured zip-up has been embraced by everyone from outdoor brands like Patagonia to high-fashion houses. The modern approach pairs these deeply practical layers with more unexpected elements—beneath a tailored overcoat, over a turtleneck with wide-leg trousers, or even with relaxed suit separates.

I acquired my first “fashion fleece” (words I never thought I’d type) last fall—a brick red number from a Japanese brand that cost approximately six times what my dad paid for his from Costco. When I wore it to brunch, layered over a white t-shirt with wide-leg twill pants and loafers, a stranger actually stopped me to ask where I got it. The satisfaction was immense, tempered only by the knowledge that my father has been wearing essentially the same item for decades without receiving a single compliment. Sometimes the only difference between “frumpy” and “fashionable” is the confidence of intentionality.

The fanny pack (or “belt bag” as marketers desperately try to rebrand it) represents perhaps the most surprising dad item comeback. Once the international symbol of the tourist father—worn exclusively at theme parks and while using a camcorder the size of a small microwave—these practical pouches have been reimagined by luxury brands and streetwear labels alike.

The contemporary approach wears them crossbody rather than at the waist, instantly transforming them from dorky to deliberate. The functionality remains identical (a place to store your wallet, phone, and keys without bulging pockets), but the execution feels completely different. I was skeptical until a three-day music festival convinced me of their undeniable practicality. Now I own two—a sleek black nylon version for everyday use and a more technical outdoor style for travel. My dad, who has worn essentially the same fanny pack to Disney World six times over three decades, finds this development hilarious. “Thirty dollars for that? Mine was eight bucks at Target!” he texted when I sent him a photo of my new acquisition. He’s not wrong, but he also tucks his t-shirts into his shorts, so we’re at an impasse.

Dad denim has also made a spectacular comeback, though with crucial updates. The light-wash, relaxed-fit jeans that dominated suburban malls in the ’90s have returned, but with more thoughtful proportions. Rather than the shapeless, pleated monstrosities that pooled around my father’s Rockports, today’s versions offer a relaxed straight leg with a higher rise and often a cropped length. Paired with loafers or boots rather than chunky white sneakers, and topped with something more interesting than a tucked-in polo, these jeans transform from sad to statement-making.

I’ve personally embraced a pair of faded vintage Levi’s 550s that would have looked right at home in my dad’s 1994 wardrobe. The difference is all in the styling—I wear them with everything from Chelsea boots and a black turtleneck to loafers and an unstructured blazer. The relaxed fit feels fresh after years of skinny jeans, and honestly, my lower body has never been more comfortable. The day I put them on and caught my reflection, I had the unsettling realization that I looked better in dad jeans at 35 than I did in spray-on skinny jeans at 25. Comfort and flattering don’t have to be mutually exclusive, a lesson my father apparently knew all along.

Perhaps the most unexpected dad trend revival is the return of the tucked-in t-shirt. This move, once the unmistakable hallmark of fathers at backyard barbecues nationwide, has been reclaimed by style-conscious men who recognize its power to create a cleaner silhouette. The modern approach pairs a simple, quality t-shirt (not the free one from your company picnic that your dad would wear) with higher-rise pants and often a statement belt.

I resisted this one for years, having spent my teenage years carefully cultivating the perfect untucked length for my t-shirts. The first time I experimentally tucked in a plain white tee with some wider-leg chinos and a vintage leather belt, my girlfriend stopped and stared. “That actually looks…really good?” she said, the surprise in her voice matching my own feelings. The proportions worked in a way I hadn’t expected, creating a cleaner line that made my casual outfit look intentional rather than lazy. When I visited home wearing this look, my dad actually pointed and laughed. “You made fun of me for that for twenty years!” His vindication was complete.

Even the practical outerwear that dominated dad closets has found new life. The fishing vest, once worn exclusively by actual fishermen and fathers who wanted sixteen pockets for unknown reasons, has been reinterpreted as a layering piece by brands from Japan to New York. The gore-tex hiking shell, formerly reserved for rainy trail excursions and coaching Little League in bad weather, now appears on runways and in streetwear collections.

I never thought I’d own a fishing vest that has never seen a fish, but here we are. Mine is navy canvas from a workwear brand, and worn over a sweatshirt with wide pants and boots, it somehow looks deliberately fashion-forward rather than like I took a wrong turn on the way to Bass Pro Shops. The multiple pockets are genuinely useful for city life (phone, wallet, headphones, notebook, pen, sunglasses), proving that sometimes dad practicality and style can peacefully coexist.

The baseball cap, long a dad staple (usually featuring a golf course logo or their favorite sports team), has been elevated from casual afterthought to considered accessory. Rather than the sweat-stained, curved-bill version my father would wear while grilling, today’s interpretation favors cleaner designs, more interesting fabrics, and a straighter brim. Worn with an otherwise polished outfit rather than as the finishing touch on full leisure wear, the cap becomes a deliberate style choice rather than a way to hide thinning hair.

My favorite cap is a simple navy wool version with no logo—miles away from my dad’s collection of various golf course caps with sweat rings around the band. But the function is identical—it adds a casual element to my outfit and requires zero thought about my hair. The wisdom of fathers, reinterpreted.

Even the sandal-with-socks combination, long the most ridiculed dad move in existence, has found redemption in fashion circles. Brands like Suicoke and Birkenstock have made the deliberately comfortable pairing acceptable, even desirable. The key difference is in the execution—think textured or patterned socks with sleek, minimal sandals rather than white tube socks with rubber slides.

I haven’t fully embraced this trend yet, though I’ve experimented with Birkenstock Bostons (technically a clog, not a sandal) worn with visible socks during transitional weather. Each time I do this, I feel my teenage self screaming in horror, but the comfort is undeniable, and when paired with otherwise considered pieces, it somehow works. My dad, who has been wearing socks with sandals to get the newspaper every Sunday morning for my entire life, deserves an apology I’m not yet ready to give him.

So what’s the secret to wearing these reclaimed dad pieces without looking like you’re actually chaperoning a middle school field trip? It comes down to three key principles:

First, it’s all about selective adoption rather than head-to-toe commitment. Wearing every dad trend simultaneously isn’t ironic or fashionable—it’s a costume. Choose one element—maybe the chunky sneakers or the fleece jacket—and pair it with more contemporary pieces. The contrast creates the tension that makes it work.

Second, proportion and fit remain crucial. Yes, silhouettes have relaxed, but there’s a massive difference between deliberately oversized and simply ill-fitting. Even the roomiest contemporary styles are cut with intention, with shoulders that hit in the right place and lengths that feel deliberate. Your dad’s clothes worked for him (sort of), but unless you share identical proportions, you need pieces cut for your body.

Finally, quality and materials elevate these formerly dismissed items. The technical fabrics, construction details, and thoughtful design of today’s “dad” pieces separate them from the bargain-bin originals. My father’s fleece was chosen purely for warmth and bought on sale; mine considers texture, weight, color, and cut—practical, yes, but also deliberately aesthetic.

The ultimate irony of the dad style resurrection is that most actual dads remain completely unaware that elements of their much-mocked wardrobes are now being sold at premium prices to their fashion-conscious sons. My father still wears essentially the same uniform he has for decades, blissfully unconcerned with the fact that his New Balance sneakers are now considered cool or that his practical outerwear choices have been vindicated by high fashion.

When I called to tell him that his style had finally become fashionable, he just chuckled and said, “So I can expect to see you at Thanksgiving in white sneakers, a fanny pack, and socks with sandals?” I told him not to push his luck. Some dad trends are still a bridge too far, at least for now. But given the rate of fashion’s rehabilitation of once-scorned items, I wouldn’t bet against eventually eating those words too.

The greatest lesson in all this might be that comfort and practicality—values dads have championed in clothing while their sons chased trends and suffered for style—aren’t inherently at odds with looking good. They just needed some refinement in execution. So next time you mock your father’s wardrobe choices, remember—in fifteen years, you might be spending good money to dress almost exactly like him. Just hopefully with better color choices than teal and purple.