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The moment I truly understood the power of alterations happened in a tiny, fluorescent-lit tailor shop in Chicago’s West Loop about eight years ago. I’d dragged my buddy Mike there on a mission of mercy. Mike—six-foot-four with the shoulders of someone who actually uses his gym membership and legs like tree trunks—had spent three desperate hours at Nordstrom trying to find a suit for his sister’s wedding. The results were… catastrophic. Either the jacket fit his shoulders but looked like a crop top, or it covered his torso but made him resemble an American football player playing dress-up in his dad’s clothes.

“Maybe I’ll just wear a nice shirt and tie,” he’d texted me, defeated.

No. Not on my watch.

We bought the suit that fit his shoulders and chest (the important, hard-to-alter parts) and took it straight to Mr. Park, a seventy-something Korean tailor who’d been altering clothes since before either of us was born. Mike stood awkwardly on a small platform, sweating under the hot lights while Mr. Park circled him like a shark, pins in mouth, muttering measurements.

Two weeks and $87 later, Mike tried on the altered suit. The transformation was so dramatic he actually said—and I swear this is a direct quote—”Holy shit, I have a waist!”

The jacket now followed the line of his torso instead of hanging like a boxy sack. The pants broke perfectly over his shoes instead of pooling around his ankles. The sleeves showed the right quarter-inch of shirt cuff instead of swallowing his hands. He looked like he’d spent a thousand bucks on a made-to-measure suit rather than three hundred on an off-the-rack one plus alterations.

When he wore it to the wedding, his style-conscious sister pulled me aside. “What did you do to my brother? He looks… good. Like, intentionally good.”

It wasn’t me. It was the oldest trick in the menswear playbook, one that’s been gradually disappearing from American style consciousness: the simple magic of alterations.

Most guys I talk to nowadays seem to think clothes come in just two categories: stuff that fits off the rack and stuff that doesn’t. It’s a bizarre misunderstanding of how garments actually work. Clothes are designed for an imaginary average person who doesn’t exist in real life. Even models—literal professional clothes-wearers—get their outfits pinned and clipped for photoshoots. The expectation that anything should fit you perfectly without modifications is fashion’s cruelest myth.

My grandfather understood this intuitively. He wasn’t a wealthy man—worked as a butcher his whole life—but the few clothes he owned fit him impeccably because he had a relationship with his neighborhood tailor. A simple working man who never made more than a modest salary had better-fitting clothes than tech bros making six figures today, and the secret wasn’t money—it was alterations.

The lost art is finally having a small renaissance, partly thanks to online custom clothing becoming more accessible, which has reminded people that clothes can—and should—actually fit their specific bodies. But custom isn’t always necessary or budget-friendly. Strategic alterations to off-the-rack items can get you 90% of the way there for a fraction of the price.

So what alterations deliver the biggest impact for the least money? After years of trial and error (and some truly questionable early experiments, like having a tailor “slim down” a vintage leather jacket in college—sorry, beautiful jacket that I ruined), here’s what I’ve learned:

For shirts, the single most transformative alteration is “darting” the back. Most men’s off-the-rack shirts are cut straight down from the shoulders, creating that billowy excess fabric that balloons around your waist when tucked in (what my tailor colorfully calls “the muffin top in reverse”). For $15-25, a tailor can add two vertical darts in the back that follow the tapering of your torso. The result is a shirt that looks custom-made.

My buddy Trevor—you remember, Hugo Boss Jr.—takes literally every shirt he buys to his tailor for this simple fix. “It’s the difference between looking like you’re wearing clothes and looking like clothes are wearing you,” he says, which is both accurate and exactly the kind of pretentious thing Trevor would say.

The second easy shirt fix is sleeve shortening, which runs $15-20. Most guys wear sleeves that are too long, which makes their proportions look off and creates a sloppy impression, especially when layered under jackets.

For pants, hemming is obvious ($10-15), but the true game-changer is adjusting the rise. If you’ve got pants that gap at the back waistband or give you that lovely “plumber’s special” effect when you bend over, a tailor can adjust the rise in the back for about $25-30. It’s one of those invisible fixes that makes everything look better without anyone being able to pinpoint exactly why.

Tapering the legs of too-wide pants ($20-25) can also bring outdated trousers into the current decade without buying all new ones. I recently rescued a pair of beautiful wool dress pants from my dad’s “donation” pile this way. They’d been sitting there because, in his words, “they make me look like a cartoon character from the ’90s.” Twenty bucks later, they’re his new favorites.

Let’s talk jackets and blazers, which is where alterations truly earn their keep. The shoulders of a jacket are like the foundation of a house—they need to be right from the start because they’re extremely difficult and expensive to alter. But almost everything else can be tweaked.

Sleeve length is the most visually obvious alteration ($25-35). A jacket sleeve should end about a quarter-inch above your shirt cuff when standing with arms at your sides. It’s amazing how many guys get this wrong, with jacket sleeves completely covering their shirt cuffs or, worse, riding halfway up their forearms.

Then there’s the jacket waist. Even moderately priced off-the-rack jackets can look custom if they follow the line of your body rather than hanging straight down. Taking in the sides ($30-50) creates that tailored silhouette that’s the hallmark of quality menswear. If you buy only one jacket but have it perfectly altered, you’ll look better than the guy with five ill-fitting expensive ones.

My most dramatic tailoring transformation happened with a navy blazer I found at a secondhand store in Boston. The fabric was gorgeous Italian wool, the shoulders fit perfectly, and the price was a ridiculous $40. But it had clearly been made for someone built like SpongeBob SquarePants—boxy, with gorilla-length arms. I spent $75 on alterations—more than the jacket itself—to shorten the sleeves, take in the waist, and adjust the button stance. The result? A $600-looking blazer for $115 total that fits better than ones I’ve paid full retail for.

There are limits, of course. Some alterations are cost-prohibitive or technically difficult. Taking in a jacket at the shoulders usually isn’t worth it. Moving the collar of a shirt is rarely successful. And adjusting the rise of pants at the front can create weird proportions. A good rule of thumb: if the alteration costs more than 60% of the garment’s price, you’re usually better off finding a different piece that starts closer to your needs.

This is why it helps to build a relationship with a skilled tailor who will tell you honestly what’s possible. Not all tailors are created equal. The dry cleaner offering hemming services is fine for simple jobs, but for anything involving restructuring a garment, you want someone who truly understands garment construction.

Finding the right tailor is a bit like dating. I went through four before finding my current guy, a second-generation Italian-American who works out of what looks like a closet in the back of an old apartment building in my neighborhood. His waiting room is literally two folding chairs, but I’ve seen well-known designers drop off samples for him to work on. When I moved apartments last year, proximity to his shop was legitimately a factor in my housing search.

The best way to test a new tailor is with a simple job first—maybe hemming pants. See if they ask questions about how you wear them (With what shoes? How much break do you prefer?). A good tailor doesn’t just execute your requests; they guide you toward what will actually look best.

Beyond the fit improvements, there’s something deeply satisfying about the resourcefulness of alterations. In an era of disposable fashion, there’s a quiet rebellion in keeping and modifying clothes rather than replacing them. My most complimented shirt is actually a hand-me-down Oxford from my uncle that was comically large until my tailor worked his magic. It cost $32 to alter and looks better than anything I could’ve bought new for three times that amount.

Alterations also give you shopping superpowers. Sales racks, vintage stores, and even hand-me-downs become viable sources of amazing clothes when you’re not limited to things that fit perfectly off the bat. That designer jacket marked down 70% because it’s the awkward size no one wanted? Buy it if it fits in the shoulders and let your tailor handle the rest.

I’ve seen too many guys dismiss potentially great pieces with “That’s not my size” when minor alterations would make them perfect. We’ve been trained to think of clothes as fixed, finished products, when they’re actually more like 80% finished products awaiting the final touches that make them truly yours.

So here’s my challenge: Take one item from your closet that you never wear because the fit is slightly off. Maybe it’s a shirt that’s too baggy, pants that are too long, or a jacket with gorilla arms. Spend the $15-30 to have it altered properly. I guarantee it’ll become one of your favorites, and you’ll be hooked on the transformative magic of this lost art.

Mr. Park retired last year. When I went to pick up my last pair of altered pants, he told me, “Young people don’t understand clothes anymore. They buy, they throw away, they buy again.” He sighed. “But you understand. You bring your friends. This is good.”

It is good. And if more of us rediscover this simple way of making ordinary clothes extraordinary, we’ll all look a hell of a lot better without spending a fortune to do it.

I turned 35 last month, and it hit me hard. Not because I’m afraid of getting older—honestly, my thirties have been way better than my twenties in almost every respect—but because I realized I was wearing the exact same outfit I’d worn on my 25th birthday. Same style of slim dark jeans. Same type of white sneakers. Same oxford cloth button-down, sleeves rolled to the elbows. The specific items were newer versions, but the look was identical. A full decade had passed, and my style had apparently been frozen in amber.

This sent me into a mild existential tailspin. Should my style have “grown up” more? Was I that guy desperately clinging to youth? Or was I just sticking with what works? I mean, it’s not like I was trying to rock skinny jeans and a graphic tee from Hot Topic. But still, the question nagged at me: Is there such a thing as dressing appropriately for your age in 2025, or is that concept as outdated as matching your belt to your shoes?

To answer this, I did what any self-respecting style writer would do—I called up men of various ages whose style I respect and asked them how their approach to dressing has evolved over the decades. The conversations were enlightening, occasionally hilarious, and surprisingly emotional.

“Your twenties are for fucking up,” said Martin, a 58-year-old creative director whose office I’ve been lowkey style-stalking for years. “Sartorially, I mean. I wore leather pants in my twenties. Actual leather pants. With fringe. There are photos. They will be burned before my funeral.” But he made an excellent point about those experimental years: “You need to get all that crazy shit out of your system. Try everything. Figure out what actually works on your body and with your personality. The guys who don’t experiment young are the ones who have midlife crises and show up in Balenciaga sneakers at 50.”

I thought back to my own twenties style journey. The unfortunate year of attempting to dress like an extra from Mad Men (too costumey). The “statement blazer” phase (too peacocky). The minimalist all-black period (too barista). Each seeming failure was actually valuable data gathering—learning what felt authentically like me versus what felt like I was playing dress-up.

Talking with guys in their twenties now, I notice they seem both more liberated and more anxious about style than my generation was. Ricky, a 24-year-old who works in tech, told me, “There are no rules anymore, which is cool but also kind of paralyzing? Like, I can literally wear anything, but then how do I know what’s right?”

What’s fascinating is how much of his anxiety stemmed not from fear of looking too young, but fear of looking prematurely old or boring. “I don’t want to dress like I’ve given up, you know? Like some generic guy in chinos.”

This gets at something important. Age-appropriate dressing isn’t about following arbitrary rules like “no jeans after 40” (bullshit) or “all men must own a navy blazer by 30” (also bullshit, though navy blazers are genuinely useful). It’s about dressing in a way that respects your current life stage without surrendering to outdated expectations of what that should look like.

For your twenties, that might mean embracing the freedom to experiment while building a foundation of versatile pieces. Every twenty-something guy I spoke with expressed the same core tension: wanting to try bold styles while also needing practical clothes for entering professional settings. The smart ones approach this by investing gradually in quality basics (good jeans, well-fitting tees, a couple of decent shirts, one proper suit) while using less expensive or vintage pieces to play with trends.

My friend David, whose style has always been impeccable, spent his twenties thrifting Italian suit jackets and pairing them with band t-shirts and paint-splattered jeans. “I was an assistant making $32,000 a year in New York. I couldn’t afford to buy a whole new professional wardrobe, but I could spend $40 on a secondhand Zegna blazer and wear it over clothes I already owned.” His style was distinctive, appropriate for creative industry events, and worked within his budget constraints.

The thirties shift happens organically for most guys, coinciding with career advancement, maybe serious relationships or family responsibilities, and—let’s be honest—a metabolism that’s becoming less forgiving. The men I know with the best style in this decade have mastered the art of looking put-together without looking stuffy.

“Your thirties are when you figure out quality over quantity,” said James, a 41-year-old architect whose minimalist-but-never-boring style I’ve always admired. “In my twenties, I had a closet full of cheap crap. Now I’d rather have three great shirts than ten mediocre ones.” He’s nailed what I think of as the thirty-something sweet spot—clothes that fit perfectly, fabrics that drape well, and a clearly defined personal aesthetic that works across multiple contexts.

My own thirties evolution has been subtle but meaningful. I’ve gradually upgraded fabrics and construction (goodbye, fast fashion; hello, year-round wool trousers). I’ve refined my color palette to what actually works with my complexion rather than whatever’s trendy. And I’ve started investing in proper shoes now that I’ve finally accepted that cheap ones both look bad and feel worse as your feet become less forgiving.

What I haven’t done is suddenly pivot to dressing “more mature” based on some arbitrary birthday threshold. I still wear sneakers, just more refined ones. I still wear jeans, just better ones with a fit that flatters my no-longer-twenty-five-year-old body. The vibe is evolution, not revolution.

This approach continues into the forties, where the best-dressed men I know have achieved something remarkable—they look appropriate and current without looking like they’re trying too hard in either direction.

“Comfort becomes non-negotiable, but that doesn’t mean giving up style,” explained Michael, a 47-year-old professor whose relaxed-but-refined wardrobe manages to look simultaneously authoritative and approachable. “I used to wear dress shoes that hurt because they looked good. Now I’ve found brands that don’t kill my feet but still look sharp. Same with everything else—the fit has to work with my actual body, not some imaginary ideal from when I was 25.”

This gets at something crucial about dressing well as you age: it requires honest assessment of your current reality, not nostalgia for your former self. The forty-something guys who look best have adapted to their changing bodies rather than fighting against them or giving up entirely. They’ve found cuts that flatter their current physiques, and they’ve developed a confident personal style that isn’t driven by fleeting trends but isn’t willfully outdated either.

By the fifties, the men with the best style have usually developed a signature look—not a uniform, exactly, but a consistent approach that feels authentic and intentional.

“I know exactly who I am now,” said Richard, a 56-year-old creative consultant who still regularly appears in street style photos despite (or perhaps because of) his silver hair. “I’m not chasing trends, but I’m not stuck in the past either. I wear what makes me feel like myself.” His wardrobe revolves around beautifully made basics with subtle details and impeccable fit, plus the occasional statement piece that keeps things from getting too predictable.

What I’ve noticed across all these conversations is that truly stylish men of any age share one quality: they dress for their current reality, not an idealized past or future version of themselves. The twenty-somethings aren’t trying to look 40, and the fifty-somethings aren’t trying to look 25. Everyone’s clothes actually fit their current bodies. They’ve all found the sweet spot where personal taste, lifestyle requirements, and physical reality converge.

The guys who struggle most with age-appropriate style are the ones fighting against their current circumstances rather than working with them. The forty-something squeezing into the same cuts he wore in college. The thirty-something who preemptively adopts an older man’s wardrobe out of some misguided attempt to look “serious.” The fifty-something who suddenly starts dressing like a hypebeast because he’s afraid of becoming invisible.

So what does this mean for my own style frozen-in-amber moment? After these conversations, I realized I don’t need to drastically change how I dress just because I’ve hit 35. But I should be honest about whether my current style truly serves my current life.

Some aspects still work perfectly—the well-fitting Oxford shirts, the quality dark jeans. But other elements could use updating. Those slim-fit chinos from 2015? They’re fighting a losing battle with my post-pandemic body. The ultra-minimal white sneakers that once felt fresh? They’ve become such a generic millennial uniform that they no longer say anything interesting.

The key isn’t to scrap everything and start over. It’s to evolve thoughtfully, keeping what works while being honest about what no longer does. To invest in quality pieces that actually fit my current body. To dress for the life I have now, not the one I had a decade ago or the one I imagine having a decade from now.

The most liberating realization from all these conversations? Age-appropriate style isn’t about following generational rules. It’s about authenticity, context, and self-awareness. The 25-year-old in a well-cut suit for the right occasion looks just as age-appropriate as the 55-year-old in well-fitting jeans and a cashmere sweater.

So I’m making small, meaningful adjustments. Embracing slightly more relaxed fits that flatter my current body. Investing in better fabrics that drape well. Focusing on versatile pieces that work for my actual lifestyle—which now includes occasional TV appearances and industry events—rather than an imagined ideal of how a 35-year-old “should” dress.

When I mentioned this approach to Martin (he of the regrettable leather pants), he nodded approvingly. “The best style advice I can give any man, at any age, is simple: dress for who you actually are, not who you think you’re supposed to be. Everything else is just details.”

That’s wisdom worth waiting 58 years for—and way more useful than any arbitrary rule about what you can or can’t wear after a certain birthday.

I got a panicked text from my buddy Chris last Thursday night. “HELP. Got promoted to senior management. Meeting with CEO Monday. Entire wardrobe screams ‘junior analyst.’ No time to replace everything. What do I do???” I could practically feel the cold sweat through my phone. Been there, man. We’ve all had those moments when our clothes suddenly feel completely wrong for where we are—or where we need to be.

The good news? You don’t need to torch your entire wardrobe and start from scratch. God knows I’ve watched too many guys do exactly that—drop three grand at Nordstrom in a panic, only to end up with expensive clothes they never actually wear because they don’t feel like “them.” What a waste. The art of the upgrade is about strategic evolution, not revolution.

When I met Chris for an emergency coffee the next morning, he looked like he’d barely slept. “I’ve been watching YouTube videos about ‘power dressing’ all night,” he admitted, stirring his third espresso. “Some guy said I need to buy everything in burgundy because it projects authority. Is that true?” I nearly spit out my cold brew. This is exactly what happens when style panic sets in—rational people start believing absolute nonsense.

First things first—I made Chris breathe and then take inventory of what he actually had. Turns out, like most guys, he owned some perfectly decent foundational pieces. Two navy suits (one with a subtle stripe), a charcoal suit he’d bought for a wedding last year, a handful of white and blue dress shirts, some basic ties, and a pair of black cap-toe oxfords that needed a polish but were otherwise fine. Not an extensive wardrobe, but also not the disaster he’d convinced himself it was at 2 AM.

The problem wasn’t the core pieces—it was how they all came together. The suits were a bit too large (he’d lost some weight), the shirts were rumpled from being stuffed in his dresser instead of hung up, and everything had this slightly neglected air about it. This is what I see all the time—guys who own the right things but aren’t wearing them the right way.

“You don’t need new suits,” I told him. “You need a great tailor.” This is upgrade principle number one, and I will die on this hill: proper fit transforms average clothes into impressive ones. I once took a $300 suit to my guy Tony in the Garment District, and after $120 of alterations, I had a random stranger ask if it was bespoke. It wasn’t the quality or the brand—it was that it fit me perfectly.

I dragged Chris to my tailor that afternoon. Tony took one look at him and immediately started pinning and tucking. “Shoulders good. Everything else? Too big. Too long. You swim in this suit,” he said in his thick Italian accent. Two hours and $200 later, Chris had left his suits to be altered by Monday morning. The transformation would be remarkable, and for a fraction of what new suits would cost.

While the suits were being sorted, we tackled upgrade principle number two: elevate your accessories. This is the fastest, most cost-effective style upgrade available to any man. “Show me your ties,” I texted him later that night. He sent photos of what can only be described as the saddest collection of neckwear I’ve ever seen—all polyester, all striped in exactly the same width, all looking like they came free with a subscription to a financial magazine in 2011.

The next morning, we hit a department store sale section and found three silk ties (navy grenadine, burgundy with a subtle pattern, and a dark green knit) for less than $100 total. “These will completely transform your existing shirts and suits,” I promised. Chris looked skeptical but trusted me. While we were there, I also made him buy two pocket squares—nothing fancy, just white linen and a navy silk with a subtle pattern. “You don’t even need to know how to fold these properly,” I told him. “Just stuff them in your jacket pocket so a bit is showing. Instant upgrade.”

The third principle of upgrading your style is what I call “refresh the foundations.” This means taking a hard look at the basics that everything else builds on. In Chris’s case, his dress shirts were fine in theory but looked like they’d been through war. We took them to the good dry cleaner—not the cheap one at the corner, but the place that charges an extra $3 per shirt and makes them look brand new. Twenty bucks later, his shirts looked crisp and professional again.

We also tackled his shoes. I grabbed the polish kit I keep in my messenger bag (yes, I’m that guy), and gave him a quick lesson in proper shoe care. His black oxfords weren’t anything special, but after fifteen minutes of conditioning, polishing, and buffing, they looked twice as expensive. “Do this every Sunday night while you watch TV,” I instructed him. “Your shoes should never look neglected.” This five-dollar solution instantly elevated his entire look.

Chris was starting to get it now. “So I don’t need to replace everything—I just need to make what I have work better?” Exactly. The fourth principle is “identify the actual weak spots.” Rather than assuming everything needs to go, figure out what specific pieces are truly letting you down. In Chris’s case, his suits, shirts, and now his ties and shoes were solid. But his belt was a disaster—cracked leather, worn buckle, obviously from a different era of his life. We found a simple replacement for $60 that instantly pulled his looks together.

His briefcase was another weak spot—a nylon laptop bag that screamed “I’m still figuring out this adult thing.” But quality leather bags are expensive, and this wasn’t the time for a major investment. So we hit up a vintage shop where I’d previously scored some amazing finds. Forty minutes of digging yielded a slightly worn but beautiful brown leather messenger bag for $90. A bit of leather conditioner from my emergency kit (again, I’m that guy), and it looked fantastic—the perfect blend of professional and personal style.

By Sunday afternoon, Chris was feeling much more confident. We’d tackled the major issues without breaking the bank, and everything was coming together. But there was one final principle of style upgrading I needed to share: “Master the details that matter.” These are the small touches that signal you’re a person who pays attention.

“When’s the last time you got a haircut?” I asked. He ran his hand through his slightly shaggy hair. “Uh, maybe six weeks ago?” Wrong answer. I immediately called my barber, who thankfully had a cancellation for late Sunday. Nothing extreme—just a clean-up that made Chris look instantly more polished. “Every four weeks, without fail,” I told him. “This is non-negotiable.” A good haircut makes even average clothes look better.

We also talked about how he actually wore his clothes. Chris had a habit of stuffing his hands in his pockets, which distorted the line of his jackets. He tended to hunch slightly. His tie knots were uneven. These subtle things might seem insignificant, but they’re actually what separates the truly well-dressed from the almost-there. We spent twenty minutes practicing proper posture, clean tie knots (four-in-hand, nothing fancy), and overall presence.

Monday morning, Chris texted me a photo of his upgraded look. The tailored navy suit fit him perfectly. The crisp white shirt was immaculate. The burgundy tie and simple white pocket square added just enough visual interest. The shoes gleamed. The new belt and vintage bag added character. But most importantly, he stood straighter and looked confident. The total cost of this transformation? Less than $500—about one-sixth what he’d been prepared to drop on new everything.

“CEO actually stopped the meeting to compliment my tie,” he texted me that afternoon. “THANK YOU.”

This whole experience reminded me of my own journey with style upgrades. When I landed my first major writing gig at Style Authority, I thought I needed to completely reinvent my look to fit in with the fashion crowd. I maxed out a credit card buying trendy designer pieces that never felt right. What actually worked was taking my existing style and just refining it—getting my favorite jeans properly hemmed, investing in better quality versions of the T-shirts I wore constantly, finding a signature accessory (in my case, vintage watches) that elevated simple outfits.

The most successful style upgrade I ever made cost exactly $0. I spent a weekend trying on literally everything I owned and getting ruthless about what actually fit and what didn’t. I ended up donating three garbage bags of clothes that were too big, too small, or just not right. What remained was less than half my original wardrobe, but everything worked. Wearing only clothes that truly fit is an instant upgrade that costs nothing but time.

My dad taught me another zero-cost upgrade trick when I was in high school. “Always roll your sleeves like you mean it,” he said, demonstrating a precise fold that looked casual but intentional. “Sloppy sleeves, sloppy man.” It sounds ridiculous, but twenty years later, I still hear his voice whenever I roll up my shirt sleeves. These tiny details make a massive difference.

The truly stylish guys I know—the ones who always look put together regardless of budget—understand that upgrades are about attention and care, not constant consumption. My friend Marcus has been wearing variations of the same basic uniform for a decade (dark jeans, oxford shirts, navy blazers), but everything fits perfectly, everything is well-maintained, and he invests in the best quality he can afford for items he wears constantly. The result is a style that feels both consistent and evolving.

One final thought on the art of the upgrade: it should be a thoughtful process, not a panicked reaction. Chris needed an emergency intervention, but ideally, you’re making small, strategic improvements over time. My approach is to upgrade one category of my wardrobe each season. This spring, I’m focusing on lightweight jackets. Last fall, it was knitwear. This methodical approach keeps me from getting overwhelmed and ensures that my style evolves organically.

The best compliment I ever received about my style came from an ex-girlfriend who ran into me years after we’d broken up. “You look exactly the same, but somehow better,” she said. That’s the art of the upgrade in a nutshell—refining rather than reinventing, elevating rather than replacing. It’s about becoming the best version of your authentic self, not trying to transform into someone else entirely.

As for Chris, he texted me again last night: “Think I’m gonna get the charcoal suit tailored next. And maybe look for some better dress shirts when there’s not a crisis.” I smiled. He gets it now. Style upgrading isn’t a one-time emergency fix—it’s an ongoing process of thoughtful refinement. And that process, much like developing your personal style in the first place, never really ends. Thank God for that. What would I write about otherwise?

Let me tell you about the weirdest day of my professional life. Last month, I found myself standing in the fluorescent-lit menswear section of a suburban Walmart at 7:30 AM on a Tuesday, wearing what my girlfriend calls my “incognito but make it fashion” outfit – a baseball cap pulled low, plain white tee, and jeans that cost more than most people’s monthly clothing budget. I was stuffing $12.88 George brand chinos into a shopping cart alongside three different Hanes multipack tees while furiously taking notes on my phone. An older employee gave me the side-eye, clearly suspecting I was either shoplifting or having some kind of breakdown. I almost showed her my website to prove I was “working,” but somehow explaining that I was a menswear journalist doing a comparative analysis of mass market basics seemed even more suspicious.

Two hours later, I was repeating the same bizarre ritual at Target, this time accumulating a cart full of Goodfellow & Co. items while a mother with twin toddlers watched me hold the same henley in navy and burgundy up to my face for a solid three minutes. “The burgundy brings out your undertones better,” she finally said, before pushing her cart away. God bless the honesty of strangers in Target.

The great American mass-market menswear experiment had begun. Why was I doing this? Well, I’d gotten like forty-seven DMs in the past month asking essentially the same question: “Dude, I’m broke but need to look decent – Target or Walmart for basics?” It’s a fair question. We all know neither store is producing heirloom-quality garments, but when your budget is tight and you need that new work shirt tomorrow, you make compromises. And honestly? The price difference between the most basic mall brands and these mass-market giants has gotten so extreme lately that even guys with comfortable incomes are wandering these aisles wondering if there’s hidden gold among the polyester blend mountains.

I’ve spent years writing about $400 Japanese selvedge denim and hand-finished dress shoes from small Italian workshops. My closet has more than a few pieces that made my accountant visibly wince during tax season. But one of my most-worn items is a simple navy cotton sweater I found at Target four years ago for $24.99 that has inexplicably outlasted merino wool versions triple its price. So I know there are gems hiding in plain sight – you just need to know what to look for and when to walk away.

The haul from my retail adventure sat in my apartment for two weeks, subjected to what my friends now call “The Reed Protocol” – wear-testing everything through multiple wash cycles, stress-testing seams, evaluating comfort after a full day’s wear, and the ultimate test: whether I’d actually reach for it again once the experiment was over. My girlfriend almost moved out when she came home to find me wearing a Walmart graphic tee with a $1,200 sport coat, but sacrifices must be made for journalistic integrity, you know?

Let’s start with what Target’s Goodfellow & Co. line gets surprisingly right: outerwear and knits. Their sweaters, particularly the cotton-blend crews and cardigans, have no business being as good as they are for $25-30. The weight is substantial, the fit is modern without being aggressively slim, and they hold up remarkably well in the wash if you ignore the care instructions asking for flat-drying (who has space for that in a New York apartment?) and just tumble dry on low. Their denim jackets and shirt jackets (or “shackets” if you insist on using that word, which I refuse to do regularly) often nail that sweet spot of looking like they cost twice as much. The secret seems to be in their color selection – slightly muted, sophisticated hues rather than primary-color brightness that screams “bargain bin.”

Walmart’s George and Time and Tru brands, meanwhile, dominate in the basics department – specifically underwear, socks, and workout gear. Their pima cotton boxer briefs ($14 for a three-pack) held up better after multiple washes than similar options at Target, and their athletic socks ($8 for a six-pack) maintained elasticity longer than competitors twice the price. The plain tees, especially the slightly thicker ones in their “premium” line, are genuinely competitive with brands charging three times as much. They’re not quite at that magical Uniqlo Supima cotton level, but they’re shockingly close for about half the price.

Where Target stumbles: dress shirts and pants. Despite Goodfellow’s generally solid reputation, their button-ups have some fit issues I just can’t get past. The collars tend to do this weird ripply thing after the first wash, and the fabric on most of their “dressy” pieces feels noticeably synthetic even when the cotton percentage is high. Their chinos start out promising but bag out dramatically at the knees after a single day’s wear. I tested their straight fit khaki against a Walmart George version of almost identical price – by lunchtime, the Target pants had developed that deflated balloon look around my knees while the Walmart ones maintained their shape better (though neither would pass close inspection in a professional environment).

Walmart’s weakest category is anything attempting to be on-trend. Their attempts at copying current styles – like the “work leisure” quarter-zips or those mock-vintage graphic tees with faux-distressing – have that unmistakable “how do you do, fellow kids?” energy. The proportions are always slightly off, with sleeves that hit at weird lengths or collars that sit awkwardly. The colors also tend toward the aggressively bright or strangely muddy with very little in between. The exception is their plain layering pieces, which can be surprisingly solid if you’re willing to try on multiple sizes to find the right fit.

The accessories at both stores deserve special mention. Target’s Goodfellow belts, particularly the braided elastic ones and simple leather options, look substantially more expensive than they are. Their sunglasses are also a hidden treasure – I’ve had $12 Target wayfarers that people assumed were Ray-Bans until they got close enough to see the branding. Walmart, meanwhile, has quietly developed a respectable collection of leather goods – their basic brown belt ($17.99) has survived regular wear for months without the dreaded cracking or peeling that usually dooms budget leather.

One category where brand loyalty makes absolutely zero sense? T-shirts. After blind wear-testing plain white tees from both retailers alongside a $45 “premium basics” version from a brand that shall remain unnamed, I literally couldn’t tell the difference after two washes. The fabric weight was nearly identical, and while the expensive one had slightly nicer finishing on the seams, it actually developed a small hole faster than either mass-market option. When a friend stopped by during this test, I made him close his eyes and feel all three shirts – he confidently identified the expensive one as “probably the cheap one” and the $8 Walmart tee as “definitely the nice one.” Fashion is weird sometimes.

Temperature plays a factor here too – both retailers mysteriously excel at opposite ends of the seasonal spectrum. Target’s fall/winter pieces generally outperform their summer offerings, with surprisingly decent sweaters, flannels, and lightweight jackets that hold up well. Walmart’s strength lies in summer basics – their performance polos and moisture-wicking tees stand up to heat and humidity better than Target’s equivalents, which tend to get that dreaded “permanent sweat stain” look much faster.

The biggest difference between the two, honestly, isn’t even the clothes themselves but the shopping experience. Target has invested heavily in store lighting and display that makes their Goodfellow line look legitimately premium at first glance. The mannequins are styled in a way that suggests “affordable but intentional” rather than just “cheap.” Walmart’s menswear section, bless their hearts, still has that unmistakable fluorescent harshness that makes everything look slightly worse than it actually is. I’ve purchased identical plain tees from both stores and consistently found that friends rate the Target version higher when they see it in the store but can’t tell the difference once the tags are removed. Retail psychology is a hell of a drug.

My very professional, very scientific testing revealed one last crucial difference: Target wins the “passing glance test” while Walmart wins the “long-term value test.” Meaning: Target clothes look better on the rack and for the first few wears, but Walmart basics often outlast them with repeated washing and wearing. If you need something that looks nice for a specific occasion or only occasional wear, Target’s your better bet. If you need something that can handle being in your regular rotation and frequent washing, Walmart’s offerings often edge ahead in durability.

So what’s the final verdict? If I had $100 to refresh my casual wardrobe and had to choose one store, I’d probably go with Target – their overall aesthetic and fit aligns better with contemporary style, and the shopping experience doesn’t make me feel like I’m in a dystopian nightmare. But the smart play is actually to cherry-pick from both: Walmart for tees, underwear, socks and workout gear; Target for sweaters, jackets, and anything you’d wear to a casual dinner with friends.

The $24.99 Target sweater that started this whole investigation is still in my rotation four years later, outlasting pieces ten times its price. And those Walmart pima cotton boxer briefs? They’re quietly taking over my underwear drawer because they’re holding up better than the fancy ones with the designer waistband. The menswear world is full of surprises if you’re willing to look past the label snobbery. Just maybe don’t tell the PR people at those luxury brands I write about that I sometimes wear Walmart boxer briefs to their fashion week events. Some industry secrets are better kept under wraps – or under my pants, as it were.

The first time I walked into a major tech campus in Palo Alto, I felt like I’d entered some bizarre social experiment where they’d eliminated all clothing choices to reduce decision fatigue. Seriously—it was like a sea of identical gray hoodies, worn jeans, and those goddamn Allbirds. You know the ones, those wool sneakers that look like potatoes with laces. I was there to interview a startup CEO for a piece on “innovation workwear” (an oxymoron if I’d ever heard one), and I stood out like a peacock at a penguin convention in my unstructured navy blazer and selvedge denim.

“Nice suit,” the receptionist smirked, despite me very clearly not wearing a suit. In Silicon Valley, anything with buttons and a collar might as well be white tie and tails.

That was 2014, the absolute dark ages of tech fashion, when Mark Zuckerberg’s normcore uniform of hoodies and tees had somehow convinced thousands of brilliant engineers that caring about your appearance was a waste of precious brain RAM. The “I’m too busy disrupting industries to think about clothes” look was practically a badge of honor. Venture capitalists would brag about owning 15 identical black turtlenecks like they’d cracked some profound life hack, as if Steve Jobs hadn’t already beaten them to that particular punch decades earlier.

But something’s shifted in the past few years. I’ve made the pilgrimage to San Francisco and its surrounding tech campuses roughly twice a year since that first visit, and I’ve watched a slow but undeniable style evolution taking place. The tech uniform hasn’t disappeared—it’s been refined, elevated, personalized. And frankly, it’s fascinating as hell to witness.

Take Eli, a product designer at one of those companies whose name has become a verb. I met him last fall at a tech conference where I was speaking on a panel about American-made goods. Four years ago, he was your standard-issue hoodie devotee. Now? He was wearing Japanese selvedge denim that he could confidently tell me was from a small Osaka mill, paired with a merino quarter-zip that probably cost more than my first month’s rent in New York. His Common Projects sneakers—a massive upgrade from the ubiquitous Allbirds—were scuffed just enough to show he wasn’t trying too hard.

“I got tired of looking like everyone else,” he told me over absurdly expensive coffee afterward. “Plus, my girlfriend kept threatening to burn my hoodie collection.”

Eli’s not alone. On my most recent trip to the Bay Area, I toured three major tech campuses and counted exactly two of those gray hoodies that had once been as common as MacBooks. Instead, I saw elevated basics—expertly tailored tees in high-quality pima cotton, Japanese oxford shirts with subtle texture, and yes, technical pants, but from brands like Outlier or Mission Workshop that actually look like regular trousers while still offering four-way stretch and enough water resistance to survive an unexpected IPO celebration champagne shower.

The tech industry’s style evolution isn’t about abandoning comfort or practicality—those remain sacred values in an industry where you might be coding for 12 hours straight. It’s about realizing that comfort and style aren’t mutually exclusive. That you can express personality through clothing choices while still being able to bike to work or sit cross-legged on the floor during an impromptu brainstorming session.

What’s driving this change? For one thing, the tech industry has grown up. The scrappy startups of 2010 are now publicly traded companies with global influence. Their employees have matured too—they’ve got disposable income, they’re settling down, they’re hitting their thirties and realizing that dressing like a perpetual college sophomore isn’t doing them any favors.

Then there’s the influx of talent from other industries. Tech has been poaching creative directors from fashion brands, marketing execs from luxury companies, and design talent from architecture firms. These transplants brought their personal style with them, quietly influencing office culture by example.

The pandemic threw another wrench in the works. When everyone went remote, the casual uniform lost its tribal significance. What’s the point of the hoodie-and-jeans combo when no one can see you below the shoulders on Zoom? As tech workers returned to offices—at least part-time—many found themselves rethinking their wardrobes entirely.

Ryan, a developer turned startup founder I’ve known for years, texted me last month: “Need help. Have investor meeting. Own zero proper shirts.” I met him at a Taylor Stitch store in San Francisco and watched his face as he tried on a well-fitting oxford for possibly the first time in his adult life.

“This doesn’t feel restrictive at all,” he said, sounding genuinely surprised. “And I look… good? Like an actual grown-up who should be trusted with millions in venture funding?”

“That’s generally the idea,” I replied.

What’s interesting about Silicon Valley’s style evolution is that it hasn’t just been about adopting traditional business attire. There’s no mass migration to suits and ties—thank god. Instead, there’s been a thoughtful hybridization. Technical fabrics meet traditional silhouettes. Performance wear gets subtle upgrades in fit and finish. Comfort remains non-negotiable, but it’s no longer the only consideration.

Take the new wave of technical blazers that have become a staple among tech execs and VCs. Brands like Ministry of Supply and Lululemon have created jackets with enough stretch to rock climb in, moisture-wicking properties for bike commuters, and machine-washable fabrics—all while maintaining the clean lines and structure of traditional tailoring. They pair perfectly with those performance chinos that dominate the landscape now, creating a look that works for investor meetings and impromptu ping-pong tournaments alike.

Even the accessories have leveled up. The status backpack isn’t just any old North Face anymore—it’s a Mission Workshop rolltop in waxed canvas or a sleek Aer laptop carrier that wouldn’t look out of place in Milan. Sneakers have gone from purely functional to carefully chosen, with brands like Hoka and On Running providing tech-forward design alongside actual performance credentials.

“I used to think caring about clothes was shallow,” admitted Sarah, a UX lead at a major streaming platform, as we discussed the evolution of her company’s unofficial dress code. “But I’ve realized it’s just another form of design, and we supposedly care about good design, right? Why shouldn’t that extend to what we put on our bodies?”

That’s the philosophical shift that’s really taken hold. The tech industry has always valued function, efficiency, and innovation. The new wave of tech style incorporates those same values—it’s just applying them to personal presentation as well as product development.

Is it perfect? Hell no. I still see plenty of questionable choices when I visit the Bay Area. There’s still that one guy in flip-flops in December. There are still logo tees from hackathons held in 2012. There are still cargo shorts that should have been peacefully laid to rest years ago.

But there’s also a growing awareness that personal style can be an asset rather than a distraction. That looking intentional doesn’t mean looking uncomfortable. That the hoodie was always more uniform than anti-uniform.

Just last week, I got an email from Eli with a photo of his company’s latest all-hands meeting. “Thought you’d appreciate the evidence,” he wrote. In the photo, at least a dozen people were wearing what I’d call elevated casual—textured knits, well-fitting chinos, minimal but purposeful accessories. Not a potato shoe in sight.

The tech uniform isn’t dead. It’s just grown up, gotten more interesting, and learned that comfort and style can coexist in the same wardrobe. Silicon Valley has finally discovered what some of us have known all along—that getting dressed can be another creative outlet, another problem to solve elegantly. And if there’s one thing tech bros love, it’s solving problems.

It started as a dare, if I’m being honest. My editor and I were having one of those late-afternoon conversations that happens when both of us are procrastinating on actual deadlines. She was scrolling through TikTok videos of fashion influencers doing “Walmart hauls” while I was pretending to fact-check a feature on luxury knitwear.

“You know what would make a great piece?” she said, not looking up from her phone. “You should dress entirely in Walmart clothes for a week and see if anyone notices.”

I laughed it off initially. Me, the guy who once wrote a 3,000-word essay on the subtle differences between Neapolitan and Florentine jacket shoulder construction, shopping at Walmart? The same guy who once spent forty-five minutes explaining the importance of goodyear welting to a clearly disinterested first date? (She didn’t call me back, shockingly.) It seemed ridiculous.

“No way,” I said. “Nobody would believe it. And besides, would anything there even fit me properly?”

My editor finally looked up, with that expression that meant I’d just accidentally pitched myself an assignment. “That’s exactly why it would work. Everyone expects Walmart clothes to look cheap and fit terribly. What if they don’t? What if it’s all about how you style them?”

Twenty-four hours later, I found myself standing in the men’s department of a massive Walmart Supercenter on the outskirts of town, feeling like an anthropologist who’d landed on an alien planet. The fluorescent lighting made everything look slightly radioactive. An announcement about a “cleanup on aisle seven” echoed through the store. And there I was, surrounded by circular racks of clothing with brand names I didn’t recognize, price points that seemed impossible, and surprisingly few screaming children considering the stereotypes.

I had set myself some ground rules: I would purchase an entire week’s worth of outfits, covering both work and weekend scenarios. Everything—from underwear to outerwear—had to come from Walmart. My budget was $200, which seemed generous until I realized my usual budget for a single decent dress shirt. To maintain some journalistic integrity, I wouldn’t tell my colleagues where my suddenly different wardrobe was coming from. I’d just dress normally and see if anyone noticed a change.

My first realization: Walmart’s clothing department is not organized like any store I’m used to shopping in. While boutiques and department stores typically arrange items by designer, style, or at least color story, Walmart seemed to follow a logic known only to its corporate overlords. Graphic tees next to dress shirts. Socks in three different locations. Jeans organized by brand rather than fit or size. It was chaos.

The second surprise: there were some legitimately interesting pieces mixed in with the expected basics. Yes, there were the plain t-shirts and simple jeans I’d anticipated, but also fair attempts at current trends—knit polos similar to ones I’d seen from J.Crew, chore coats that wouldn’t look out of place in a workwear boutique, and some decent-looking sweaters.

I started with the foundational pieces—two pairs of jeans, chinos in navy and khaki, a selection of t-shirts and button-downs, a couple of sweaters, and a surprisingly decent-looking twill jacket that gave off light chore coat vibes. The biggest shock came at the register: my entire pile of clothing—enough for multiple outfit combinations for a full week—came to $172.43. I’ve spent more than that on a single pair of jeans.

Back home, I laid everything out on my bed for inspection under less forgiving lighting. The quality differences compared to my usual wardrobe were immediately apparent upon closer examination. The fabric of the button-down shirts was thinner with looser weaves. The jeans had none of the substantial heft I was used to. The stitching was functional rather than refined, with occasional loose threads and uneven seams.

But here’s the thing—from more than two feet away, none of those quality issues were particularly visible. Which led me to my first strategic realization: this experiment would be all about styling and fit. If I could find pieces that fit reasonably well and combine them thoughtfully, maybe the lower quality wouldn’t be immediately obvious to the casual observer.

Monday morning arrived, and with it, my first day of the Walmart experiment. I opted for a relatively simple look: dark jeans from their George brand ($16.98), a light blue Oxford-style button-down ($12.98), and a navy cotton-blend sweater ($13.96) layered over top. I completed the look with my own leather boots and belt, since shoes and accessories weren’t part of the experiment—a concession my editor had granted after I sent her a photo of Walmart’s footwear section.

Walking into the office, I felt like I was wearing a sign that said “I’M DRESSED IN WALMART CLOTHES ASK ME ABOUT IT.” Every fiber of my being was conscious of the thinner fabric against my skin, the slightly off proportions of the collar, the way the sweater already seemed to be stretching at the cuffs after a single wear. But remarkably, nobody seemed to notice anything different.

The real shock came during an editorial meeting when Lisa from the digital team actually complimented my outfit. “That blue is a good color on you,” she said casually. “Is that sweater new?”

I mumbled something noncommittal, simultaneously pleased and horrified. Was my regular wardrobe so forgettable that a $14 Walmart sweater was actually drawing positive attention?

Emboldened by surviving the first day without being fashion-shamed, I got more adventurous on Tuesday. I wore the twill chore jacket ($26.96) over a simple white t-shirt ($5.98 for a two-pack) with the khaki chinos ($17.98) and my own minimal white sneakers. Walking to the coffee shop where I often write before heading to the office, the barista who knows me by name actually said, “You look nice today—date later?” When I told my editor this during our check-in call, she laughed for a solid thirty seconds.

By Wednesday, I was conducting an accidental master class in how context and confidence affect perception. The clothes themselves were undeniably lower quality than what I typically wore, but styled thoughtfully and worn without apology, they were passing not just unnoticed but actually receiving compliments.

The khaki chinos, while lacking the refined details and perfect taper of my usual brands, actually fit my waist and thighs better off the rack than some much more expensive pairs I owned. The twill jacket, which I’d initially dismissed as a poor man’s chore coat, was developing a nice worn-in look after just a couple of wears and paired surprisingly well with both casual and slightly dressier outfits.

Thursday brought the first significant challenge: a client meeting where I’d normally wear one of my better blazers. Walmart did have sport coats, but even I couldn’t pretend they were passable quality upon close inspection. Instead, I assembled a “dressy without a jacket” look: the navy chinos, a white button-down, and a simple merino-blend v-neck sweater in charcoal ($16.98). In what was becoming a pattern, not only did the outfit pass without comment, but the client actually mentioned that I always dressed well. I had to excuse myself to the restroom to have a silent existential crisis.

By Friday, I’d moved from embarrassment to a strange sort of liberation. My budget outfit—jeans, a simple navy polo from their “performance” line ($11.98), and the twill jacket—felt comfortable and looked put-together. When a colleague asked where the jacket was from, I almost told the truth before catching myself and vaguely mentioning “just a place at the mall.”

For Saturday brunch with friends, I wore the straight-fit dark jeans with a surprisingly decent cream-colored cotton sweater ($18.94) that had elbow patches which, while clearly synthetic, actually added a touch of professorial charm. My friend Marcus, who regularly drops designer names in casual conversation about his weekend plans, asked if the sweater was new. When I nodded, he said, “Nice texture. J.Crew?”

I almost choked on my avocado toast.

Sunday was the final day of the experiment—a casual day of errands and grocery shopping where I wore the light wash jeans, a henley from their “premium” line ($9.98), and the twill jacket that had become a surprise MVP of the week. At the farmer’s market, a stranger actually stopped me to ask where my jacket was from. I mumbled something about “online” and scurried away, simultaneously proud of how the outfit looked and mortified at the thought of admitting its true origin.

When the week ended, I sat down to take stock of what I’d learned. The physical garments themselves had performed better than expected in some ways and exactly as expected in others. The jeans, while initially comfortable, had already begun to stretch out significantly, losing their shape by day three of wearing. The t-shirts were thinning where my messenger bag strap crossed my chest. The sweaters were pilling under the arms. These clothes were not built to last.

But the more profound realization was about how much of our perception of clothing quality is influenced by context, styling, and confidence. When I wore these budget items with the same care and attention to fit and combination that I applied to my more expensive clothes, most people couldn’t tell the difference at a glance. The details that obsessive style enthusiasts like me fixate on—stitching density, fabric weight, perfect proportions—simply don’t register with the average observer.

Does this mean I’m giving up my carefully curated wardrobe of thoughtfully made pieces? Absolutely not. Quality ultimately matters, especially over time. After just one week, several items were already showing signs of wear that my regular clothes would withstand for years. The environmental and ethical implications of ultra-fast fashion are impossible to ignore for anyone paying attention. And there’s still a tangible difference in how well-made clothing feels on the body, even if others can’t see it.

But the experiment did challenge my sometimes-dogmatic views about the necessity of spending more for style. There’s a middle ground between “disposable fashion” and “investment pieces” that I hadn’t fully appreciated. For certain categories—especially simple items like t-shirts, casual sweaters, or chinos that see hard wear—the calculus of quality versus price might deserve reconsideration.

More importantly, it reminded me of something I’ve always believed but sometimes forget in my enthusiasm for craftsmanship details: great style is ultimately more about how you wear clothes than what you wear. Fit, proportion, color combination, and appropriateness to the setting matter more than the price tag or the label when it comes to making an impression.

The most humbling moment came the Monday after my experiment ended, when I returned to my normal wardrobe. I wore one of my favorite combinations—Japanese selvedge denim, a made-in-Italy oxford shirt, and an English lambswool sweater, all in complementary shades of blue and cream. The total cost of this single outfit was roughly ten times what I’d spent on an entire week of Walmart clothes.

Not a single person commented on it.

When I finally revealed the experiment to my colleagues over lunch, their reactions ranged from disbelief to begrudging respect. “That blue sweater was from Walmart?” Lisa asked, genuinely shocked. “I almost asked where you got it because the color was so good.”

My editor, of course, was insufferably pleased with herself. “Maybe your next feature should be about how no one actually notices what you’re wearing as much as you think they do,” she suggested. I chose not to dignify this with a response.

The Walmart clothes now hang in a separate section of my closet. Some items—the chore jacket, the cream sweater, the surprisingly decent chinos—have earned at least occasional rotation in my casual weekend wardrobe. Others have already been donated after just a few wears, their quality too compromised for even experimental purposes.

But the lesson remains: with enough attention to fit, color, and context, it’s possible to look stylish at almost any price point. The difference between a $20 sweater and a $200 one isn’t invisible, but it might be less noticeable to the outside world than fashion enthusiasts want to believe.

Just don’t ask me to try the shoes. Even style journalism has its limits.

The precise moment I knew I had a problem was standing in the security line at O’Hare, watching a family of four check fewer bags than I had packed for a solo long weekend in Miami. The father—efficiently dressed in performance chinos and one of those travel shirts with hidden pockets for your passport—glanced at my overstuffed roller bag and sizeable “personal item” tote with what I can only describe as pity. His wife was somehow bringing just one tasteful, compact duffel for herself and both children, while I had packed like I was fleeing the country with the crown jewels.

I’d like to tell you this was an unusual occurrence. That I’m actually a minimalist packer who ruthlessly edits his vacation wardrobe to the bare essentials. But the truth is, I have historically approached packing with the philosophy that it’s better to have options. Too many options. Options for weather that the forecast doesn’t predict, for impromptu formal events that might spontaneously materialize, for the possibility that I might suddenly develop an entirely new personal style mid-trip.

It’s ridiculous, I know. The reality is I end up wearing maybe 40% of what I pack, lugging the rest around like some kind of fashion security blanket. Meanwhile, my girlfriend can pack for a two-week European vacation in a bag that fits under the seat, containing a wardrobe that somehow looks freshly pressed and appropriately on-point for every single activity and setting. It’s witchcraft, honestly.

The breaking point came last year when airlines somehow made their already draconian baggage policies even more restrictive. Suddenly, my strategy of “I’ll just pay for a checked bag” didn’t seem so clever when that bag now cost almost as much as the flight itself. Add in the indignity of waiting 45 minutes at baggage claim (if your luggage shows up at all) while all the smart carry-on people are already halfway to their destinations, and I knew something had to change.

So I embarked on what my friends now call “The Great Packing Reformation”—a complete overhaul of how I approach vacation wardrobes. Through extensive trial and error (and several embarrassing over-packing incidents), I’ve developed a system that lets me pack for up to a week in just a regulation carry-on, with clothes that actually work together and accommodate most situations a normal human might encounter. No more bringing four pairs of shoes “just in case.” No more packing three sport coats for a beach vacation (yes, I really did this once).

The foundation of efficient packing is brutal honesty about what you’ll actually be doing on vacation. Not what you imagine you might do in some alternate-universe version of your trip where you’re suddenly invited to dine with local aristocracy, but what you will realistically be doing based on your itinerary, destination, and—most importantly—your actual habits.

For years, I packed aspirationally rather than realistically. I’d bring running shoes and workout clothes for a trip where my only planned exercise was lifting cocktails to my mouth. I’d pack blazers and dress shirts for beach destinations where the fanciest restaurant still allowed flip-flops. I was packing for some imaginary version of myself who suddenly develops habits and preferences completely different from my normal life just because I’ve crossed state lines.

The first step in my reformation was creating what I call a “reality check” list before any trip. It forces me to map out what I’ll actually be doing each day and night, with specific attention to dress codes and activities. Beach day? Museum visit? Nice dinner? Casual drinks? Hike? Work meeting? Once I have this honest assessment, I can build a wardrobe that covers these actual needs rather than hypothetical scenarios.

This might seem obvious, but I can’t tell you how many men I know who pack with a vague sense of “well, you never know what might happen” rather than looking at what’s actually on the schedule. Trust me, if you unexpectedly get invited to a formal gala in Barcelona, you can either buy something there (shopping in a new city is part of the fun!) or politely decline. The possibility doesn’t justify hauling a tuxedo across the Atlantic.

The next foundation of carry-on success is embracing the reality of doing laundry on the road. I know, I know—laundry on vacation feels like defeat. But modern quick-dry fabrics and the ubiquity of hotel laundry services (or even just a bathroom sink and some travel detergent) mean you can bring half as much and just wash key items halfway through. I now pack assuming I’ll do at least one small load of laundry on any trip longer than four days.

This was a psychological hurdle for me. Something about planning to do laundry felt like I was somehow “failing” at vacation. But once I embraced it, my luggage literally halved in size. Instead of seven t-shirts for a week-long trip, I bring three or four high-quality ones that can be washed in a hotel sink and dry overnight. The fifteen minutes it takes to wash a few key items is far less painful than dragging an oversized checked bag through crowded streets or paying excess baggage fees.

With those foundations in place, let’s talk about the actual strategy of building a vacation wardrobe that fits in a standard carry-on while still giving you enough flexibility to look and feel good throughout your trip.

The most crucial concept is the color palette. Before I pack a single item, I now decide on a limited color scheme—usually no more than three core colors plus one or two accents. This ensures that virtually everything in my bag works with everything else, creating exponentially more outfits from fewer pieces.

For a recent week in Portugal, I built everything around navy, olive green, and white/cream, with burgundy as an accent. Every single item I packed—from t-shirts to shorts to the one light jacket—fit within this palette. The result was being able to get dressed in seconds each morning, knowing that any combination would work together visually. No more staring at an open suitcase full of clothes that somehow don’t go with anything else I’ve brought.

This approach requires discipline. That statement piece with the bold pattern might be amazing, but if it doesn’t work with at least three other items in your bag, it’s staying home. Save those one-off outfits for when you’re not living out of a suitcase. Vacation is when versatility becomes your best friend.

Next comes the brutal math of multi-functionality. Every single item in your carry-on should serve at least two purposes or work in at least two distinct settings. That linen button-up isn’t just for dinner—it’s also a beach cover-up. Those chino shorts work for daytime sightseeing but can handle an evening out with the right shirt. The lightweight sweater layers under your jacket for cooler evenings but works on its own during the day.

When I’m debating whether to pack something, I now ask myself: “What are the specific scenarios where I’ll wear this?” If I can only name one occasion, it doesn’t make the cut. This rule alone has probably saved me from bringing dozens of “just in case” items that would have spent the entire vacation compressed at the bottom of my bag.

The shoes question is where most men’s packing falls apart. I used to be a four-pair-minimum guy: sneakers for walking, loafers for casual evenings, dress shoes for nice dinners, and maybe boat shoes or sandals for beach days. That’s literally half your carry-on space just for footwear. Now I aim for two pairs, three absolute maximum.

For most trips, I’ve found that one pair of minimal, comfortable sneakers (think plain white leather that can dress up or down) and one pair of versatile loafers or driving shoes cover 95% of vacation scenarios. For beach trips, I’ll add flip-flops, which take up virtually no space. The key is choosing shoes that bridge dress codes—those crisp white sneakers can handle a museum day but also work with chinos for dinner. The loafers dress up with a button-down for evening but don’t look fussy with shorts during the day.

This approach requires letting go of strict formal/casual distinctions that matter more at home than on vacation anyway. Most vacation destinations (outside of business trips) have more relaxed dress codes than you might assume. That fancy restaurant in Positano is probably full of people wearing clean sneakers with their linen shirts. The rooftop bar in Barcelona isn’t expecting wingtips. Pack for the reality of your destination, not the formality of your hometown.

The fabric question is another game-changer for efficient packing. I’ve gradually replaced many of my vacation clothes with versions in wrinkle-resistant, quick-drying, and in some cases, odor-resistant technical fabrics. Not the obvious “I’m wearing performance gear” kind, but the new generation of technical fabrics that look like normal cotton, linen, or wool but perform much better on the road.

Brands like Lululemon, Ministry of Supply, and Proof now make shirts, pants, and even blazers that can handle being rolled up in a suitcase, worn multiple times, and even given a quick sink wash if needed. They might cost more initially, but they’ve transformed my packing strategy by giving me more wears per item with less maintenance. My favorite travel button-up looks like Oxford cloth but dries in a third of the time and emerges from my bag without needing ironing.

And since we’re talking about fabric, let’s address the rolling versus folding debate. After extensive experimentation, I’ve found that a hybrid approach works best. Thinner items like t-shirts, underwear, and swimwear get rolled tightly. Button-ups and pants get folded along their natural seams and laid flat. Jackets, if I bring them, get turned inside out, folded once, and placed on top. This maximizes space while minimizing hard creases.

For a standard week-long vacation in a temperate climate, my carry-on now typically contains: three t-shirts, two button-ups, one light sweater or long-sleeve tee, one pair of jeans or trousers, two pairs of shorts, one pair of swim trunks (that can double as casual shorts), five pairs of socks and underwear, two pairs of shoes, and possibly one light jacket depending on the forecast. Everything works together colorwise, and most items serve multiple functions.

That might sound minimalist, but it’s more than enough for a week when you consider that you’ll be wearing one complete outfit while traveling, leaving only six days to cover from your bag. With mix-and-matching and perhaps one quick load of laundry midweek, this creates plenty of options without hauling half your closet across the country.

Let’s talk about the toiletry situation, which can quickly consume valuable carry-on space if you’re not careful. I’ve ditched most of my full-size products in favor of either travel sizes or solid versions—solid cologne, shampoo bars, and deodorant all take up less space and eliminate liquid concerns for TSA. I also no longer bring “just in case” toiletries for scenarios I’m unlikely to encounter. Most hotels provide the basics, and anything else can be purchased at your destination if truly needed.

My dopp kit used to be the size of a small briefcase. Now it’s a compact pouch containing only what I know I’ll use daily. The space savings is significant, and I’ve yet to encounter a toiletry emergency that couldn’t be solved with a quick stop at a local pharmacy. Does anyone really need three types of hair product on vacation anyway? (My answer used to be yes, embarrassingly.)

A word about outerwear, which can be the carry-on killer. For most trips, I now wear whatever is bulkiest on the plane—be it a light jacket, sweater, or both. This not only saves suitcase space but also gives me layers to adjust to often-frigid airplane cabins. If I absolutely need a heavier coat for the destination, I’ll wear it while traveling even if it means being slightly overdressed at the departure airport. Better that than sacrificing half your luggage space.

For cold-weather destinations, I’ve embraced the technical advantages of modern lightweight down and synthetic insulation. My winter travel jacket packs down to the size of a water bottle but provides serious warmth. It’s not what I’d choose for style points at home, but for travel, the space savings is worth the minor aesthetic compromise. And honestly, newer technical outerwear has come a long way in the looks department.

Here’s a travel hack that’s saved me repeatedly: pack one simple, fool-proof outfit that makes you feel great right in the top of your suitcase. Something that requires zero thought and works for most situations. This becomes your emergency outfit for when laundry plans fall through, when unexpected weather hits, or when you’re just too tired to think about what to wear. Mine is usually dark jeans, a navy button-up, and clean white sneakers—basic but put-together enough for most scenarios.

This brings me to my most controversial packing opinion: it’s better to slightly underpack than overpack. If you find yourself short an item, you can almost always purchase it at your destination—and often, that locally purchased piece becomes a unique souvenir with an actual story behind it. Some of my favorite items of clothing came from vacation shopping emergencies: the linen shirt bought in Lisbon when an unexpected heatwave hit, the sweater from a small shop in Copenhagen when I underestimated the evening chill.

Contrast this with the psychological weight of dragging around excess clothing you never wear. I’d rather spend twenty minutes and fifty bucks buying an extra t-shirt locally than haul four “just in case” shirts across the globe and back untouched. The math on this just makes sense, both financially and in terms of travel enjoyment.

So what does this all look like in practice? Let me break down my actual packing list for a recent seven-day trip to Italy in late spring, all of which fit in a standard carry-on plus a small backpack:

In my carry-on: Two short-sleeve button-ups (one olive, one subtle pattern with navy/white), two t-shirts (one white, one burgundy), one long-sleeve henley (navy), one pair of jeans (dark blue), one pair of chino shorts (olive), one pair of swim trunks that double as casual shorts (navy), one lightweight quarter-zip sweater (navy), five pairs of underwear, three pairs of socks, one pair of loafers (brown), toiletry kit, and one packable rain jacket just in case.

Worn on the plane: Minimal white sneakers, light blue button-up shirt, comfortable chinos in a stone color, watch, belt.

That’s it. Everything worked with everything else. I did one small sink wash of t-shirts and underwear halfway through. I felt appropriately dressed for every situation, from casual pizzerias to a surprisingly upscale vineyard tour. And most importantly, I never had to check my bag, roll it over cobblestone streets, or hoist it onto crowded trains.

The greatest luxury in travel isn’t bringing your entire wardrobe—it’s the freedom of movement that comes with packing light without sacrificing style. It’s breezing past the baggage claim while the checked-bag people wait in purgatory. It’s easily navigating public transit instead of requiring taxis due to unwieldy luggage. It’s the physical and mental lightness that comes from carrying only what you actually need.

My girlfriend, who has always been a packing minimalist, watched my transformation with amusement. “Welcome to the light side,” she said as I proudly displayed my single carry-on before our last trip. “Only took you what, fifteen years of overpacking?”

She’s not wrong. But I like to think all those years of bringing too much have given me a unique appreciation for bringing just enough. And if I occasionally find myself short an item? Well, that’s just an opportunity to bring home something new with an actual travel story attached to it—which beats another unworn shirt that spent its vacation in the dark confines of an overstuffed suitcase any day.