Tag: updated

My apartment flooded last year. Not like, “oops, spilled my Nalgene on the bathroom floor” flooded. More like “upstairs neighbor’s bathtub somehow relocated itself into my living room at 3 AM” flooded. I woke up to the sound of my ceiling giving birth to Niagara Falls and managed to save exactly three things before the rest of my possessions became very expensive sponges: my laptop, my grandfather’s watch, and weirdly, a hamper of clean laundry I’d been too lazy to put away.

The insurance company was actually pretty decent about replacing most things. But my clothing collection? That was a different story. Trying to catalog and justify the replacement value of fifteen years of accumulated menswear to a skeptical claims adjuster named Gary was… humbling. “So you had seventeen oxford cloth button-downs in slightly different shades of blue?” he asked, peering at me over his glasses. “And you needed all of them?” I started to explain the subtle but critical differences between Supima cotton and regular oxford cloth, the importance of different collar rolls, the—actually, you know what? I stopped myself. Because Gary was right. I didn’t need seventeen nearly identical shirts. Nobody does.

Living out of a suitcase for the next six weeks while my apartment was being renovated was strangely liberating. I had exactly five outfits, a leather jacket, and two pairs of shoes to my name. And somehow, miraculously, I still managed to dress appropriately for everything from client meetings to dates to a friend’s gallery opening. Nobody at work noticed I was wearing the same navy blazer twice a week. My girlfriend (now fiancée) didn’t seem to care that I only had one pair of jeans. The world kept spinning.

It got me thinking—how much of my wardrobe was actually essential? How many pieces did I truly need to cover 95% of life situations? And more importantly, what would a genuinely American capsule wardrobe look like? Not a European minimalist aesthetic transplanted to New York, but something that works for the realities of American life, climate, and social expectations from Maine to California.

So I did what any menswear obsessive with insurance money burning a hole in his pocket would do—I started rebuilding my wardrobe from scratch with a strict “essentials only” policy. My goal was 15 pieces, not counting underwear, socks, or workout clothes. Just 15 versatile items that could cover everything from casual weekends to business meetings to weddings.

The process was brutal. I’d find myself reaching for non-existent garments out of habit. “Where’s my… oh right, it got soaked in dirty ceiling water and now it’s gone forever.” But gradually, something interesting happened. I stopped missing most of it. In fact, having fewer options made getting dressed faster, more intuitive, and somehow more satisfying.

Here’s what made the cut—the only 15 items an American man actually needs to be appropriately dressed for 95% of life situations:

1. Dark indigo jeans (straight cut or slim-straight)
I went with Levi’s 501s because they’re literally the most American garment ever created. Mid-rise, not too slim, not too relaxed. They work equally well in Montana or Manhattan. The trick is finding the wash that hits that sweet spot between too dark (looks like you’re trying too hard) and too distressed (looks like you’re stuck in 2003). A medium-dark indigo with minimal fading is the most versatile.

2. Khaki chinos
Bill’s Khakis or LL Bean make the most authentically American versions. I chose a medium khaki—not too yellow, not too gray—with a straight leg that can be cuffed in summer or break slightly over boots in winter. Mine have a bit of a military influence with a slightly higher rise than most modern versions. They pair with literally everything else on this list.

3. Charcoal wool trousers
This was my one concession to formal situations. Slightly tapered with a clean break at the shoe, they’re office-appropriate but don’t scream “suit separates.” The key is finding a four-season weight wool that doesn’t cook you in summer or leave you freezing in winter. Avoid super-skinny cuts—they’ll be dated before you know it.

4. White oxford cloth button-down shirt
Brooks Brothers still makes the definitive version, but J.Crew’s version is about 80% as good for half the price. The one non-negotiable feature is a properly rolled collar that buttons down without laying flat against the shirt. It should create a gentle arch that frames your face. Sounds fussy, but it’s the difference between looking like you understand classic American style and looking like you bought whatever was on the mannequin.

5. Light blue oxford cloth button-down shirt
Same specifications as above, just in the most versatile color known to menswear. I probably wear this shirt twice as often as anything else on the list. It goes with absolutely everything and somehow manages to be both casual and put-together simultaneously.

6. White dress shirt (spread collar)
For actual formal situations, interviews, weddings, funerals, and the rare dinner that requires a tie. Nothing fancy here—just a well-fitted white broadcloth shirt with a moderate spread collar that accommodates different tie knots. Skip the button-down collar for this one; a proper dress shirt needs an unfettered collar stand.

7. Gray crewneck sweatshirt
The most underrated American classic. Mine’s from Champion—basic, unadorned, slightly oversized in that 1960s athletic department way. It works with jeans, chinos, under a jacket, over an oxford…basically everything. The neck should be sturdy enough to hold its shape and the body roomy enough to layer over a button-down comfortably.

8. Navy merino crewneck sweater
The Swiss Army knife of the wardrobe. Dress it up with trousers and a collared shirt, dress it down with jeans, layer it under a jacket in winter. I found mine at Uniqlo for approximately the price of two cocktails in Manhattan, and it’s held up beautifully for years. The key is finding a mid-weight merino that doesn’t pill excessively.

9. Navy blazer (year-round weight)
If I could only save one item from my wardrobe in another flood, it might be this. A properly fitting navy blazer makes jeans look intentional and dress trousers look relaxed. The most versatile version has a natural shoulder (minimal padding), two buttons, notch lapels, and patch pockets. Mine’s from Southwick—an old-school American maker that nails the Ivy League aesthetic without the stuffy European details.

10. Charcoal suit
The only true suit on the list needs to work for job interviews, weddings, funerals, and any situation where you need to project competence and respect. Charcoal is more versatile than navy for a single suit because it transitions from day to evening better and reads as appropriately serious for somber occasions. Two-button, notch lapel, with trousers that have a clean break at the shoe.

11. Olive field jacket
The most versatile outerwear piece for three-season wear. Mine’s from Filson—a cotton tin cloth version of their traditional field jacket with handwarmer pockets and a drawable waist. It’s rugged enough for weekend hikes but structured enough to wear over a button-down and chinos for casual Friday. The olive color is key—it’s essentially a neutral that pairs with everything.

12. Brown leather boots
Alden’s Indy boot is the gold standard, but Grant Stone makes a nearly identical version for half the price. The key is finding a plain or cap toe style with minimal ornamentation in a medium brown that can be dressed up or down. They should be comfortable enough to walk miles in but polished enough to wear with dress trousers in a pinch.

13. Brown penny loafers
The most versatile shoes in American menswear. Bass Weejuns are the original, but I splurged on a pair from Oak Street Bootmakers that has developed a gorgeous patina over the years. They work with shorts in summer, with jeans year-round, and even with a suit in less formal settings. The key is finding an almond toe shape that’s neither too pointy (too European) nor too rounded (too clunky).

14. White leather sneakers
The concession to modern casual dress codes. I went with a pair of German Army Trainers—they’re sleeker than most American athletic shoes but still have a utilitarian vibe that works with the rest of this wardrobe. Simple, clean, versatile. They work with literally everything else on this list except the suit (though even that pairing is increasingly acceptable in creative industries).

15. Navy knit tie
If you’re only going to own one tie, this is it. A textured silk knit in navy with a squared-off bottom. It dresses down a suit for less formal occasions, dresses up jeans and a blazer, and has just enough texture to look intentional rather than corporate. I found mine at Drake’s, but J.Crew makes a perfectly acceptable version for a third of the price.

And that’s it. Fifteen items that cover everything from Saturday morning coffee runs to Monday boardroom meetings. No statement pieces, no seasonal one-offs, just versatile classics that work in combination with each other.

Now, I’m not saying this is all you should ever own. My own wardrobe has gradually expanded beyond these 15 pieces over the past year (I’m still a menswear editor, after all—occupational hazard). But whenever I find myself standing in front of my closet paralyzed by too many options, I return to this core capsule.

The beauty of this approach is how thoroughly American it is. These aren’t minimalist Scandinavian basics or tailoring-heavy Italian essentials. This capsule acknowledges that Americans need clothes that transition from casual to formal, that most of us don’t dress up daily, and that practicality matters just as much as style. It’s built around icons of American design—the OCBD, the sweatshirt, the field jacket, the penny loafer—that have proven their versatility over decades.

What I’ve learned from living with less is that constraints breed creativity. Having only 15 core pieces forces you to consider how each one interacts with the others. It eliminates decision fatigue. It makes packing for trips absurdly simple. And perhaps most importantly, it connects you to a lineage of American style that transcends trends.

I’m not suggesting you manufacture a flood to force yourself into wardrobe minimalism (though I do have my former upstairs neighbor’s contact info if you’re interested). But I am suggesting that most of us could cut our closets by 70% and actually dress better as a result. Start with these 15 pieces—or your own version of this core capsule—and see how it feels to have fewer, better options.

Oh, and as for Gary the insurance adjuster? He ended up approving my claim for the seventeen blue button-downs. But I only replaced two of them. The rest of that money went toward a trip to Maine with my fiancée, where, ironically, it rained the entire time. Some lessons you just have to learn twice.

My buddy Mark showed up to our lunch last Tuesday wearing what can only be described as sartorial schizophrenia. Up top? A crisp light blue Oxford shirt and a perfectly nice navy knit tie. But below the table line? Faded joggers and—I swear to God—actual running shoes. Not even the kind pretending to be acceptable casual footwear. Literal performance running shoes with those horrific neon yellow accents that scream “I might decide to train for a 5K during this business meeting!”

When I pointed this out (gently, I’m not a monster), he looked genuinely confused. “What? This is how I’ve been dressing for work for like two years now. Camera-ready on top, comfort on the bottom.”

And there it was—the perfect encapsulation of our current business casual crisis. Two years of Zoom meetings has created a generation of professional mullets: business up top, pandemic party down below. We’ve collectively forgotten how to dress for actual human interaction in professional settings, and now we’re all wandering into offices looking like we got dressed in the dark while half-remembering advice from a grandfather’s outdated style manual.

I’ve been fielding frantic texts about this exact problem for months. “Jack, I have to go into the office tomorrow for the first time since 2020. WHAT DO PEOPLE WEAR NOW???” Or my personal favorite, from my college roommate who now works at a tech-adjacent financial firm: “Is it weird that I don’t remember how to tie a tie? Like, physically, my fingers have forgotten. Help?”

Let’s be clear about something: business casual was already a confusing disaster before the pandemic hit. The term originated in the 1970s and gained steam during the 1990s when companies like Dockers (yes, the khaki people) actively pushed for more casual workplace attire—coincidentally while selling exactly the kind of clothes that would qualify. By the early 2000s, most American offices had some version of business casual dress code, with widely varying interpretations depending on your industry, location, and the personal preferences of whatever executive happened to care most about employee appearance.

But post-pandemic? We’re living in the Wild West of workplace attire. I recently visited five different offices in New York for a piece I was researching. In one finance-adjacent tech company, I saw a guy in a full suit sitting next to someone wearing cargo shorts and Birkenstocks. At a media company, the range spanned from “could be going to a nightclub later” to “might be currently homeless.” A traditional insurance firm still had most employees in dress shirts and slacks, but even they had outliers in jeans and sneakers. No one knows what the rules are anymore because the rules no longer exist in any coherent form.

So what’s a confused corporate drone to do? After talking with HR directors, C-suite executives, and yes, the poor souls trying to navigate this mess daily, I’ve compiled some updated guidelines that won’t make you look like you got dressed in the dark or are desperately clinging to 2019.

The most consistent advice I heard was: context matters more than ever. Sarah, an HR director at a major consulting firm, told me that they’ve formally relaxed their dress code but with a critical caveat: “We tell people to dress for their day. Client meeting? More formal. Internal work day? More casual. Working from home? Just please wear clothes during video calls, we’ve had incidents.”

Those “incidents” remained unspecified and I chose not to press for details that would certainly leave emotional scars.

This “dress for your day” approach seems to be the emerging consensus across industries. The old blanket rules are dead, replaced by a more nuanced understanding that your outfit should match your activities. Revolutionary concept, I know.

But this creates a new challenge—you need multiple modes in your work wardrobe, often within the same day. This was driven home to me during a recent coffee meeting with Alex, a creative director at an ad agency who showed up looking sharp as hell in dark jeans, a textured blue blazer, and suede chukkas. When I complimented his look, he laughed and pulled out his phone to show me a selfie from two hours earlier—same guy, completely different outfit of joggers and a hoodie.

“Had a morning of internal Zoom calls, then this client coffee, then back to the office for production reviews where I’ll probably get dirty looking at prototypes,” he explained. “So I keep a couple of outfit changes at the office now. My assistant says I’m like Batman but for clothes.”

This kind of strategic wardrobe planning—once the domain of fashion editors and celebrities—is becoming the norm for regular corporate workers navigating hybrid schedules. The guy who used to keep an emergency tie in his desk drawer now has an entire backup outfit or two.

So what specifically constitutes appropriate business casual in this brave new world? After shadowing workers across various industries and interviewing people who make hiring and firing decisions (the ultimate dress code enforcers), I’ve identified some emerging patterns.

For men, the biggest shift is in structure and formality. The matched suit is increasingly rare outside client-facing roles in conservative industries. In its place is what I’m calling “high-low tailoring”—combining more formal pieces (like a good blazer) with more casual ones (like refined jeans or chinos). The trick is maintaining a balanced equation: the more casual one element, the more refined the others need to be.

This means if you’re wearing jeans (which are increasingly acceptable), they should be dark, well-fitted, and unstressed—no conspicuous fading or artificial distressing, for god’s sake. Pair them with a proper shirt—not a t-shirt unless you’re in creative or tech—and ideally a blazer that’s been tailored to fit you properly. Footwear has relaxed significantly, with clean leather sneakers now widely acceptable, though traditional leather shoes still read as more professional.

My friend Darren, a VP at a financial services firm, formulated it perfectly: “The old rule was don’t wear anything you’d wear to mow the lawn or go to a club. That still applies, but now there’s this whole middle territory that’s opened up.”

That middle territory includes previously controversial items like sneakers, jeans, and even the occasional hoodie—though styled dramatically differently than their weekend counterparts. The key differentiator? Quality, fit, and context.

For example, sneakers are increasingly common, but they should be clean, minimal, and ideally in a subdued color palette. We’re talking Common Projects, not the Air Jordans you wear to shoot hoops on Saturday. A fine gauge merino hoodie under a blazer can work in creative environments, while a graphic hoodie with dropped shoulders reads as too casual even in tech.

The most egregious business casual sins I’ve observed recently aren’t about specific garments but about how they’re worn. Shirts with visible stains. Pants that clearly haven’t been washed in several wears. Shoes that are scuffed beyond recognition. The pandemic seems to have lowered our collective standards for maintenance, perhaps because we grew accustomed to no one seeing us below the shoulders.

This was hilariously demonstrated when I spoke with Jamie, an executive assistant at a law firm, who implemented a new policy after the return to office: “We now keep a stain stick, lint roller, and shoe shine wipes in every conference room because too many people were showing up to client meetings looking like they’d just eaten a sandwich in their car, which they probably had.”

Another pandemic-specific issue is fit. Many people’s bodies changed during lockdown, yet they’re trying to squeeze into pre-pandemic wardrobes. Nothing undermines an otherwise decent outfit like pulling buttons or waistbands cutting in like a tourniquet. Marissa, a tailor who works with several Wall Street firms, told me her business has exploded with alteration requests as people return to offices: “Half my clients need everything let out. The other half lost weight from stress and need everything taken in. Nobody fits in their 2019 clothes anymore.”

My biggest observation after months of research into this shifting landscape? The dividing line between “acceptable” and “unacceptable” now has less to do with specific categories of clothing and more to do with intent and execution. A well-chosen, properly fitted casual outfit reads as more professional than ill-fitting formal wear. An outfit constructed with obvious thought will always surpass something reflexively thrown on.

This was perfectly illustrated during a visit to a tech company where I observed two employees with superficially similar outfits—jeans, sneakers, button-downs—but radically different impressions. One looked sharp and intentional; the other looked like he’d gotten dressed in the dark. The difference wasn’t what they were wearing but how they were wearing it.

The good news in all this confusion? There’s unprecedented freedom to develop a personal style that works for your industry and body while still hitting the mark professionally. The bad news? That takes way more thought than just reaching for the old uniform of chinos and a blue button-down.

My advice for anyone navigating these uncharted waters: invest in versatile pieces that can dress up or down depending on how you combine them. A good navy blazer works with everything from grey dress trousers to dark jeans. Clean white sneakers can work with most casual office looks while maintaining comfort. A selection of well-fitted button-downs in different weights and textures can be the foundation of countless outfits.

Most importantly—and I cannot stress this enough—everything should actually fit your current body. Not the body you had in 2019. Not the body you hope to have after another six weeks of your current fitness kick. Your actual, present-day body deserves clothes that fit properly.

As we settle into whatever “normal” eventually becomes, I suspect we’ll see the emergence of new workplace style tribes rather than a return to unified dress codes. The traditionalists who maintain pre-pandemic formality. The comfort-first contingent who’ve adapted office-appropriate versions of athleisure. The fashion-forward who use the office as a personal runway. And of course, the perpetually confused who’ll keep texting people like me at 11 PM asking “is this tie too wide for an 11 AM presentation?”

To which I’ll reply, as always: “It depends—who’s your audience, and what do you want them to think about you?” Because ultimately, that’s what all this boils down to. In a world without clear rules, the real question is what story your clothes are telling—intentionally or not—about who you are professionally.

As for my friend Mark and his mullet outfit? He sheepishly admitted that he’s been keeping dress shoes and proper trousers in his desk drawer, changing into them for important meetings and then back into his comfort clothes afterward. “It’s exhausting,” he sighed. “Sometimes I miss suits. At least then I always knew what to wear.”

I didn’t have the heart to tell him that’s exactly what we’ll be wearing again in about five years. Fashion is cyclical like that. In the meantime, I’ll keep answering those panicked texts one confused office worker at a time.

Last Tuesday, I was sitting at my favorite coffee shop in Williamsburg when I watched an interesting scene unfold. Two guys, probably in their early thirties, walked in wearing almost identical outfits – dark jeans, gray t-shirts, white sneakers, and navy bomber jackets. They clearly didn’t know each other. In fact, when they noticed their mirror-image wardrobes, there was this moment of awkward recognition, like when you show up to a party and someone’s wearing the same shirt. Guy #1 immediately zipped his jacket to create some visual difference. Guy #2 shoved his hands in his pockets and hunched slightly, physically trying to change how his identical clothes looked on his body.

I almost laughed out loud. Not because there’s anything wrong with their outfit formula – it’s practically the official uniform of thirty-something urban American men for good reason. It works. But their mutual discomfort at being caught in the same basic template was fascinating. They’d both independently arrived at exactly the same “safe” combination that’s become the default American casual look.

This is the paradox of contemporary menswear: we’ve settled on a broadly accessible casual uniform that looks decent on most guys, but its very ubiquity has created a new problem. How do you stand out when everyone’s working from the same basic template? How do you elevate standard American casual beyond, well, standard?

The good news is that upgrading your casual game doesn’t require dramatic changes or becoming “that guy” in attention-grabbing clothes. The most effective improvements happen through subtle adjustments to fit, fabric, proportion, and details – the elements most guys don’t consciously notice but that collectively create a massive difference in how polished the final result appears.

I’ve spent years studying how certain men manage to look exponentially better than others while technically wearing the same categories of clothing. The secret is rarely about spending more (though quality does matter). It’s about understanding the nuances that separate basic from refined within the established American casual framework.

My own journey beyond basic started about twelve years ago when I was an assistant at my first magazine job. I wore the same uniform as everyone else – jeans, t-shirts, occasional button-downs, sneakers or boots depending on weather. But our style director, Marcus, wore essentially the same categories of clothing while somehow looking significantly more put together. One day, in a moment of frustration, I finally asked him how he did it.

“Come with me,” he said, leading me to the fashion closet (the magical room where sample clothes lived). He pulled out two seemingly identical white t-shirts and handed them to me. “Feel the difference.”

One was thin, slightly rough, with a collar that was already starting to warp after presumably just a few washes. The other was substantial, with a soft hand and a collar that felt somehow… reinforced? The difference was immediately apparent through touch, yet to the casual observer, they were just two white tees.

“The first one costs $15 for a three-pack,” Marcus explained. “The second is $45 for one. But the second one will look good after thirty washes. The first will look like garbage after five. Which costs more per wear?”

That moment changed how I thought about casual clothing forever. The identical silhouettes could deliver dramatically different results based on quality factors most guys never consider. Since then, I’ve cataloged the specific differences that separate basic casual from elevated casual, creating a practical upgrade path that works within the established American aesthetic without veering into try-hard territory.

Let’s break it down category by category:

The humble t-shirt seems simple, but it’s where subtle improvements deliver the most dramatic upgrades. The difference between a basic tee and an elevated one comes down to three factors: fabric weight, collar construction, and cut. A quality tee uses heavier cotton (usually 5-7 oz compared to the 3-4 oz standard), has a collar that’s either reinforced or cut to lay flat naturally, and is proportioned specifically to be worn alone rather than as an undershirt. The upgrade path is simple: find a brand that nails these elements in a price point you can justify (Uniqlo’s U collection hits the sweet spot of quality vs. cost), buy multiples in neutral colors, and replace them when they start to deteriorate. The difference is subtle but significant – your basic outfit template immediately looks more intentional.

The standard button-up shirt gets its upgrade through fabric texture and fit precision. While basic casual often features smooth oxford cloth or pinpoint cotton in slightly oversized fits, the elevated version incorporates more interesting textures – slubby chambrays, dobby weaves, brushed flannels with depth – in cuts that actually match your proportions. The shoulders should hit at your shoulder bones (not droop beyond), the body should follow your torso without excess billowing, and the sleeves should end exactly at your wrist bone when unbuttoned. Finding shirts that fit this precisely often requires trying numerous brands until you identify your match, but the search pays off through a dramatically improved silhouette.

Jeans are perhaps the most complex upgrade because the signifiers of quality have become so confused in modern marketing. Price absolutely doesn’t correlate with how good denim looks in the wild. Instead, focus on three elements: fabric stability, cut accuracy, and details. Quality denim maintains its shape throughout the day rather than bagging at the knees and seat. The cut should create a clean line from hip to hem without excess fabric pooling at the ankle or squeezing in the wrong places. And details like reinforced belt loops, chainstitched hems, and clean finishing separate elevated denim from basic versions. My personal upgrade path led from Levi’s to Japanese selvedge brands, but the important part was finding denim that maintained its intended shape through all-day wear.

Casual jackets – whether bombers, chore coats, or denim jackets – make their leap to the next level through material choice and structural integrity. Basic versions use flat, uniform fabrics with fusible internal structure that creates a cardboard-like hand. Elevated versions incorporate materials with inherent character (waxed cotton that patinas, wool with visible texture, leather that develops personality) and construction that creates shape through proper stitching rather than glued interfacing. They start good and get better with age, while basic versions start okay and deteriorate steadily.

Footwear is where upgrade investments deliver the most visible returns. The difference between basic and elevated casual shoes isn’t about formality – it’s about material quality and proportional refinement. Compare a $80 faux leather sneaker to a $200 full-grain leather version with the same silhouette. The materials flex differently, catch light differently, and age differently. The proportions on quality footwear tend to be more considered – slightly sleeker without becoming dressy, with intentional design elements rather than cost-cutting compromises. My first significant upgrade was from mass-market desert boots to a hand-stitched pair from Oak Street Bootmakers. Same basic style, dramatically different execution.

The most frequently overlooked upgrade? Proper garment care. Basic casual often looks basic because clothes are maintained through a standardized laundry cycle that gradually degrades fabrics, warps structures, and flattens textures. Elevated casual incorporates appropriate maintenance – hanging knits to dry rather than machine drying, using proper leather conditioners, washing denim less frequently to maintain its character. This alone can extend the life of clothes by years while maintaining their intended appearance.

Beyond specific garment categories, the two biggest differences between basic and elevated casual are proportional harmony and color sophistication.

Proportional harmony means considering how garment lengths and volumes work together rather than treating each piece in isolation. Basic casual often features elements that create unintentional conflict – a shirt that’s too long with a jacket that’s too short, creating awkward layering, or slim jeans paired with oversized tops that throw off the overall balance. Elevated casual considers the complete silhouette, ensuring that proportions create intentional harmony or intentional contrast, never accidental discord.

Color sophistication separates the men from the boys in casual dressing. Basic casual relies heavily on primary colors, stark contrasts, and safe combinations. Elevated casual incorporates subtle tonal play, thoughtful texture mixing, and an understanding of color temperature. Instead of navy and white (the most basic combination in menswear), try navy and off-white, or better yet, navy and ecru. Instead of gray and black, explore charcoal and olive. The path from basic to sophisticated color often involves moving from saturated primary shades toward more complex, slightly muted versions of those colors.

The beauty of these upgrades is their subtlety. You won’t look like you’re trying too hard. You won’t suddenly appear “dressed up.” You’ll simply look like a more polished, intentional version of casual American style. The guy who gets the second glance rather than blending into the sea of sameness.

My personal upgrade journey took years of trial and error, with plenty of missteps along the way. I wasted money on designer versions of basic items that weren’t actually better, just more expensive. I went through a regrettable phase of thinking that adding unnecessary details (extra zippers, contrast stitching, decorative elements) was the path to elevation. Eventually, I learned that true upgrade comes from quality fundamentals executed with precision, not from superficial flourishes.

The transformation happens gradually – replacing one category at a time as budget allows, developing your eye for quality markers, building relationships with brands that align with your proportions and aesthetic. Start with the elements you wear most frequently. If t-shirts are your daily staple, upgrading those first delivers the most immediate impact on your overall appearance.

I’ve watched countless friends make this journey, moving from basic to elevated casual without changing their fundamental style approach. The universal reaction? People notice something’s different but can’t quite identify what. They’ll say, “You look great – did you lose weight?” or “That color really works on you,” without realizing they’re responding to the improved quality, fit, and proportion. It’s the best kind of style upgrade – subtle enough to feel authentic but significant enough to change how you’re perceived.

My favorite example is my friend Eric, who wore the standard uniform of jeans, tees, hoodies and sneakers for years. His gradual upgrades – slightly better denim with a more flattering cut, tees with proper weight and collar structure, minimalist sneakers in quality leather rather than canvas, a french terry hoodie that maintained its shape – transformed how he presented without changing his essential style. At his wedding last year, his father-in-law pulled me aside and said, “When they started dating, I thought he was a slob. Now he always looks put together. What changed?” Everything and nothing, I explained. Same template, better execution.

So the next time you find yourself face-to-face with your style doppelgänger in a coffee shop, resist the urge to zip up or hunch over. Instead, take mental notes on the specific differences between your identical-but-not-identical outfits. The weight of his t-shirt fabric. The break of his jeans over his sneakers. The way his jacket sits across his shoulders. Those subtle differences contain all the information you need to elevate your casual game beyond basic.

And after all, in the land of the basic, the slightly-less-basic man is king.

I’ve got this Yankees cap that’s been through hell and back with me. Faded navy, brim perfectly curved (not bent, never creased—I’m not a monster), logo just weathered enough to say “I’ve had this for years” without looking homeless. It’s traveled to nineteen countries, been washed exactly twice, and survived being left behind at a bar in Montreal where I had to tip the bartender an embarrassing amount to ship it back to me. My girlfriend—now ex, unrelated to the hat situation—once said, “It’s like your comfort blanket but for your head,” which wasn’t meant as a compliment but I took it as one anyway.

That hat has seen me through three apartments, two career changes, and countless bad hair days. It’s been worn to interviews, first dates, and my sister’s rehearsal dinner (briefly, until my mother snatched it off my head with the speed and precision of a falconer). There’s something about a well-worn baseball cap that becomes an extension of your personality, less an accessory than a piece of your daily uniform.

You know what’s weird? For such an iconic American item, we rarely talk about baseball caps with the reverence we give other menswear classics. Denim gets scholarly books and museum exhibitions. Military jackets have their origins traced like biblical genealogy. But baseball caps? They’re so ubiquitous, so democratic, so goddamn common that we barely register their cultural significance.

Which is nuts when you think about it. In what other country can the same accessory be worn by the president on vacation, a billionaire tech mogul avoiding paparazzi, a construction worker on site, and a high schooler heading to class? The baseball cap is America’s great equalizer—worn by literally every demographic across political, economic, and social divides. It might be the last truly bipartisan piece of American culture that hasn’t been ruined by internet discourse.

My fascination with baseball caps started, predictably enough, with actual baseball. My dad took me to Wrigley when I was seven, and after watching the Cubs lose spectacularly (some traditions are sacred), he bought me my first cap—an adjustable wool blend that was way too big and kept falling over my eyes. I wore it until the wool pilled and the sweatband disintegrated, less out of team loyalty than because it became my thing. By high school, I’d graduated to a rotation of caps that my mother called my “identity crisis collection”—Yankees (despite zero New York connections), vintage Expos (team didn’t even exist anymore), Lakers (never watched a game), and a truly regrettable Von Dutch phase that we will not be discussing further.

What I didn’t realize then was that I was participating in an American tradition that stretches back to 1860 when the Brooklyn Excelsiors first donned what would evolve into the modern baseball cap. It wasn’t until the 1940s that the structured, stiff-brimmed version we know today became standardized. By the ’70s, caps had escaped the baseball diamond and entered everyday wardrobes, and the ’90s saw them become a full-blown cultural phenomenon. Spike Lee’s red Yankees cap—a fashion disruption so profound the Yankees organization initially hated it—sparked a revolution of non-traditional cap colors that reverberates today.

What makes a great cap? After decades of obsessive wear and probably thousands of dollars spent (don’t tell my accountant), I’ve developed some thoughts. First, it’s about shape. The perfect cap has a slightly domed crown, not too tall, not too shallow. The brim should be moderately curved—not flat-brimmed like you’re auditioning for a 2008 rap video, and not crimped in the middle like you’re a college baseball coach. The closure—whether snapback, strapback, fitted, or (god help us) velcro—is a matter of personal preference, though I’ll die on the hill that a metal clasp strapback is superior for adjustability and longevity.

Materials matter too. Wool caps are traditional but can be hot and itchy. Cotton twill is the gold standard for everyday wear. Performance fabrics have their place for actual athletic activities but rarely develop the character of natural materials. And don’t get me started on cheap polyester caps with ventilated backs—unless you’re actively working as a trucker in 1983, there’s no excuse.

But here’s the truth that cap manufacturers don’t want you to know: the best baseball caps are the ones that have been broken in by time and wear. No “distressed” factory finish can replicate the authentic patina of a cap that’s been worn through summer storms, shoved in back pockets, and left on sun-baked dashboards. The perfectly broken-in cap is earned, not bought.

Last year, I interviewed Mark, a pattern maker at one of the last American factories still producing caps for MLB teams. “A good cap is architectural,” he told me while showing me around the factory floor in upstate New York. “Six panels forming a dome, a brim that both shades and frames the face, a sweatband that keeps the whole thing in place. Simple, but not easy to get right.” He picked up a cap from the production line and pointed to the stitching around the eyelets. “See how these ventilation holes are reinforced? That’s where most cheap caps fail first. The details matter.”

The details do matter, but what’s most interesting about baseball caps is how they’ve transcended their athletic origins to become vehicles for self-expression, tribal affiliation, and even political signaling. A red MAGA cap communicates something very different than a frayed Patagonia cap, which says something different than a flat-brimmed Yankees cap worn slightly askew. We read these signals instinctively, making assumptions (sometimes unfair ones) about the wearer’s politics, social class, and cultural affiliations.

I’ve seen this firsthand while traveling internationally. Nothing says “American” quite like a baseball cap. In Tokyo, a local shop owner instantly pegged me as American before I’d said a word, pointing to my Mets cap (a brief diversion from Yankees loyalty during a particularly promising season) and saying, “New York?” In Paris, a waiter rolled his eyes at my cap/blazer combination in a way that somehow conveyed several centuries of Franco-American tension. And in a small town in Italy, an elderly man pointed to my Yankees cap, gave me a thumbs up, and said “DiMaggio!” – proving that some cultural touchstones transcend language.

So how do you incorporate a baseball cap into a grown-up wardrobe without looking like you’re having a midlife crisis or heading to a frat party? It’s all about context and contrast. A well-worn cap with a navy blazer, oxford cloth button-down, and chinos creates a high-low mix that feels effortless rather than juvenile. The key is making it look intentional, not like you just forgot to take your hat off indoors (though, between us, the “must remove hats inside” rule feels increasingly archaic outside of fine dining and religious settings).

For weekend wear, the cap is a no-brainer with jeans and t-shirts, but it also works with more elevated casual pieces. One of my favorite combinations is a simple gray cap with a camel topcoat during fall—something about the structured tailoring paired with the casual cap creates a tension that’s more interesting than either piece would be alone.

The one area where I draw the line? Formal events. Despite what Justin Timberlake tried to make happen in 2007, the suit-and-cap combination remains firmly in “no” territory. Some rules exist for a reason.

The baseball cap market has exploded in recent years, with options ranging from $5 gas station specials to designer versions that’ll set you back hundreds. Todd Snyder’s collaborations with historical cap makers like Ebbets Field Flannels offer heritage quality with updated fits. Standard issue brands like ’47 and American Needle hit the sweet spot of quality and affordability. And yes, if authenticity is your thing, you can still buy the exact caps worn by major league players, though be prepared for a break-in period that’ll test your patience—those structured wool caps are stiff as cardboard until they’ve weathered a few rainstorms.

But my honest advice? Find a cap that means something to you—your hometown team, a place you’ve traveled, a brand or organization you believe in—and then wear the hell out of it until it becomes uniquely yours. The best cap isn’t the most expensive or the rarest; it’s the one that feels like an extension of yourself, that you reach for without thinking, that friends and family associate with you even when you’re not wearing it.

Mine will always be that Yankees cap, despite having no personal connection to the Bronx and being unable to name more than three current players on the roster. After fifteen years of consistent wear, it’s less a fashion choice than a part of my identity. The blue has faded to a color that doesn’t exist on any pantone chart, the sweatband has molded perfectly to my head, and the MLB hologram sticker has long since disappeared. It’s traveled with me from Chicago to New York to Los Angeles and back again, a constant companion through job changes, relationships, and life transitions.

There’s something comforting about having an item that remains unchanged while everything else evolves. In a world where we’re constantly curating and adjusting our image, a well-worn baseball cap is refreshingly authentic—you can’t fake a decade of sun exposure and sweat stains. It’s perhaps the most honest piece in many men’s wardrobes.

So here’s to the baseball cap—the democratically priced, universally flattering, historically rich accessory that manages to be both quintessentially American and entirely personal. Whether you’re covering a bad hair day, showing team loyalty, or just adding the finishing touch to an otherwise solid outfit, the right cap is more than just headwear. It’s a statement piece that, ironically, requires no explanation at all. Just don’t ask to borrow mine. Some things aren’t meant to be shared.

Let’s get real for a second. Those Banana Republic models—with their perfect V-torsos, broad shoulders tapering to narrow waists, and legs that somehow look a mile long even in relaxed-fit chinos? I’ve spent enough time in this industry to know that half of them have their clothes pinned within an inch of their lives backstage. The other half won some kind of genetic lottery that the rest of us weren’t even invited to enter. Meanwhile, I’m standing in a BR fitting room with three different sizes of the same sweater, wondering which version of “not quite right” I’m going to settle for today.

I’ve had a complicated relationship with Banana Republic over the years. It was the first “grown-up” store I shopped at with my own money in college, convinced their merino sweaters would transform me into a sophisticated adult who had his life together. (Narrator: They did not.) I’ve watched them pivot from safari-inspired catalogs to wannabe J.Crew to whatever their current “elevated basics with a twist” identity is supposed to be. Through it all, I’ve maintained a drawer full of their t-shirts and a closet with at least two of their blazers at any given time.

But here’s the thing—I’m built like a former high school athlete who discovered beer and desk jobs. My shoulders are relatively broad, but so is my midsection. My thighs have enough muscle to make slim-fit pants a challenge but not enough definition to make it look intentional. In short, I’m shaped like a normal American guy, which means I’m nothing like the mannequins in their windows.

After roughly 47 Banana Republic shopping trips over the past decade (yes, I counted for this article), I’ve developed a mental catalog of what actually works for non-model body types. This isn’t about “bigger” sizes—it’s about understanding which of their cuts and styles actually accommodate the way most of us are built, regardless of the number on the tag.

First, let’s talk shirts, which seem like they should be the simplest but somehow become a physics-defying challenge. Their standard dress shirts come in three fits: Slim, Standard, and Relaxed. The names would suggest a clear progression of roominess, but that would be too logical. Instead, they’ve created a system where Slim is designed for people who apparently don’t have internal organs, Standard fits absolutely nobody correctly, and Relaxed has enough fabric to double as a weekend sailing spinnaker.

The trick I’ve found is to ignore their categorization entirely and focus on specific models. Their “Tech-Stretch” shirts, despite typically being labeled as Standard fit, actually have the most forgiving cut through the midsection while still maintaining some shape. The “Non-Iron” shirts, despite supposedly being the same fit as regular cotton versions, somehow manage to be tighter across the chest and shoulders—avoid these unless you enjoy the sensation of your shirt trying to win a wrestling match with your armpits all day.

Their “Untucked” shirts deserve special mention for solving a problem most of us didn’t realize we had. For years, I thought I just had an unusually long torso because standard dress shirts would come untucked if I so much as glanced at my shoelaces. Turns out, BR’s standard shirts are simply cut with enough length to create a small fabric parachute around your waist. The Untucked versions eliminate this problem entirely—they’re my go-to recommendation for guys who are tired of looking like they’re wearing their dad’s hand-me-downs.

The Oxford cloth button-downs are a different story entirely. For reasons known only to their design team, these are cut with shoulders seemingly intended for Olympic swimmers while simultaneously being cropped shorter than their other shirts. The result? A shirt that makes you look like you’re wearing your little brother’s hand-me-ups. Size up if you must have one, but be prepared for a tent-like fit through the body.

Now, let’s tackle pants, which is where BR really shines if you know what to look for. Their chinos come in approximately 73 different named fits (slight exaggeration), but the only ones worth considering for regular human legs are the “Athletic Tapered” and the “Relaxed.” Forget the Skinny, Slim, and even the Straight fits unless you have the legs of a distance runner.

The Athletic Tapered is the holy grail for guys with any muscle in their thighs—roomy through the seat and thigh, then tapering below the knee for a clean silhouette. They look tailored without requiring you to perform elaborate contortions to sit down. I have four pairs in different colors, and they’re the workhorses of my business casual wardrobe.

BR’s jeans deserve special mention for being consistently inconsistent. The same size and style can vary dramatically between colors and seasons. I once bought two identical pairs of their Rapid Movement jeans in different colors, only to discover one fit perfectly while the other seemed to have been designed for someone three inches shorter with one larger leg. My advice? Always try them on, even if you’re repurchasing what should be the same jean. And if you do find a pair that fits perfectly, buy two, because they’ll almost certainly change the cut by the time you wear through your first pair.

Their dress pants present a similar challenge. The “Slim” dress pants should be called “Compression Therapy for Your Femoral Artery.” Meanwhile, the “Standard” fit is actually reasonable through the thigh but bizarrely wide at the ankle, creating a subtle bell-bottom effect that no one is asking for. Your best bet is to find their “Athletic” cut dress pants when available, then have the bottom tapered by a tailor if needed.

The sleeper hit in BR’s pants lineup is their traveler pant. With a deceptive amount of stretch and a more generous cut than their standard chinos, these are wildly comfortable while still looking sharp. The waistband also has just enough give to accommodate those days when lunch turns into a three-course affair. They’re my go-to for flights and client meetings that involve sitting for extended periods.

Sweaters and knitwear are perhaps BR’s most frustrating category for the average-built man. Their merino sweaters, while buttery soft and available in an impressive range of colors, are cut with what I can only describe as “aspirational sizing.” The mediums assume you have the proportions of a teenager, while the larges add width without adding enough length. The result is a choice between “sausage casing” or “crop top,” neither of which is the look most of us are going for.

The exception here is their chunky cotton sweaters and cardigans, which tend to have a more forgiving silhouette. The beefier material means they hold their shape better and don’t cling to every contour of your torso. Their shawl-collar cardigans, in particular, have been consistently well-proportioned over the years, with enough room in the chest and arms for normal movement while maintaining a clean line.

Outerwear is where Banana Republic genuinely excels for a variety of body types. Their jackets and coats typically have a more generous cut than their other offerings, perhaps acknowledging that people might want to wear actual clothes underneath them. Their mac coats and topcoats have consistently fit well off the rack, with shoulders that accommodate a normal human frame and enough room through the chest to move without feeling restricted.

Their bomber jackets deserve special praise for actually fitting the way a bomber should—slightly oversized and comfortable rather than the vacuum-sealed interpretation many brands offer. I’ve had a BR navy bomber for four years now, and it’s still my go-to for travel and weekend wear precisely because it accommodates whatever I’m wearing underneath without making me look like the Michelin Man.

Let’s talk about their suits and blazers, which present a unique challenge. BR’s jackets typically come in the same trinity of fits as their shirts—Slim, Standard, and Relaxed—but again, these labels are more suggestions than definitions. Their “Slim” suit jackets aren’t actually as constrictive as you might fear, with enough room through the chest and back for a normal range of motion. The real problem comes in the sleeves, which seem designed for men with the arms of a T-Rex—short and disproportionately small compared to the chest size.

The Standard fit solves the arm circumference issue but introduces a boxy cut that does no favors for anyone not built like SpongeBob. Your best bet is to try their “Smart” collections, which despite the marketing gibberish about performance fabrics, tend to have the most balanced proportions—trimmer than their Standard fit but not as restrictive as their Slim.

For blazers specifically, look for their “knit blazers” or anything with stretch in the description. These tend to be more forgiving across the back and shoulders, where traditional BR blazers can feel constrictive even when the chest measurement is correct. I’ve found their cotton-blend summer blazers fit more generously than their wool options, perhaps acknowledging that summer bodies aren’t always as sculpted as winter aspirations.

A word on accessories, which might seem size-agnostic but actually aren’t. BR’s belts run consistently small—size up from your normal pant size or prepare for disappointment. Their scarves, on the other hand, are generously sized and work well for anyone who wants both function and style from winter accessories.

One of BR’s most underrated categories for non-model bodies is their performance wear line. These items—stretchy polos, technical fabric pants, etc.—seem designed with actual human movement in mind rather than just looking good in catalog poses. The polos, in particular, have enough give through the shoulders and chest to accommodate guys who occasionally lift something heavier than a smartphone.

Here’s my ultimate Banana Republic shopping hack for regular bodies: shop the sale rack at the end of the season. Not just because of the obvious financial benefit, but because these are often the items that didn’t sell well at full price—frequently because they were cut more generously than their standard offerings. I’ve found some of my best-fitting BR pieces this way, items that clearly didn’t work on their target demographic of urban twenty-somethings but fit my regular-guy frame perfectly.

I should also mention their foray into “extended sizes,” which has been hit-or-miss. Rather than simply scaling up their existing designs (which rarely works well), their better offerings in this category seem to be proportioned differently, acknowledging that larger guys aren’t just bigger versions of slim guys but might have different proportional needs entirely.

After all these years shopping their collections, I’ve developed a simple rule of thumb for Banana Republic fitting: if it looks perfect on the mannequin, it’s probably going to be problematic on a regular human being. The pieces that appear slightly relaxed or even a touch rumpled on their displays? Those are your best bet for real-world wearability.

Is shopping at Banana Republic worth the fitting room gymnastics for the average American man? For certain categories, absolutely. Their Athletic Tapered chinos, casual outerwear, and performance-oriented pieces offer solid value and genuinely good fit for normal bodies. Their basic sweaters, Oxford shirts, and slim-anything should be approached with caution and realistic expectations.

The real trick is understanding that the “aspirational” aspect of BR’s branding extends to their sizing—they’re selling not just clothes but the idea that you might transform into that catalog model if you just buy the right merino V-neck. Once you make peace with the fact that no amount of Italian cotton is going to give you the proportions of their photography subjects, you can focus on finding the genuinely good pieces that work for your actual body.

And if all else fails? That’s what tailors are for. Even with BR’s moderate price point, budgeting an extra $15-20 for simple alterations can transform an almost-right garment into a workhorse of your wardrobe. After all, the secret those catalog models aren’t telling you is that literally nothing fits anyone perfectly off the rack—not even them.

The first pair of American-made jeans I ever owned were a complete accident. I was twenty-two, broke as hell, and had stumbled across a pair of raw selvedge Cone Mills denim at a secondhand store in the East Village. They were stiff as cardboard, at least one size too small, and cost more than I’d typically spend on an entire week’s worth of meals. But there was something about that little red selvedge line peeking out from the cuff that I couldn’t resist. The fact they were made in North Carolina—according to the tag that I studied like it contained the secrets of the universe—seemed impossibly exotic to my young, fashion-obsessed brain.

I bought them, of course. Wore them religiously, washed them rarely (sorry to everyone who had to sit next to me on the subway during that particular phase), and watched with something approaching religious devotion as they faded to match the exact contours of my life. When they finally gave out—a catastrophic crotch blowout while I was bending to pick up a coffee mug in front of an important editor, because the universe has a sick sense of humor—I genuinely considered framing them.

That was fifteen years and God knows how many pairs of jeans ago. In that time, I’ve watched American denim production go through a renaissance, a boom, and now what feels increasingly like a last stand. The closure of Cone Mills’ White Oak plant in 2017 felt like a personal affront to every denim head I knew. Texts flew between my friends in the industry—”Did you hear?” “Are you stocking up?” “Is this really happening?”—like we were discussing a death in the family rather than a fabric factory shutting down.

Which, in a way, it was. For over a century, American-made denim represented something fundamental about our national identity—hardworking, authentic, built to last. The fabric of America, both literally and metaphorically. Yet one by one, the looms fell silent as production moved overseas, lured by cheaper labor and fewer regulations. Finding jeans actually made in the USA became increasingly like hunting for vinyl records in the age of Spotify—a niche passion for purists and nostalgics.

But here’s the thing about Americans—we’re stubborn as hell. While mass production has largely left our shores, a dedicated group of brands, artisans, and enthusiasts has kept the flame alive. These are the people who refuse to believe that American denim is just a nostalgic concept rather than a living tradition.

I’ve spent the past six months tracking down every American jeans manufacturer still operating domestically. I’ve visited tiny workshops in Los Angeles, converted warehouses in Detroit, and even a former tobacco processing facility in Kentucky now humming with the sound of vintage Union Special machines. What I found was both heartbreaking and deeply hopeful—an industry simultaneously on the brink and on the cusp of reinvention.

Let’s start with the old guard. Though Cone Mills’ iconic White Oak plant closed, their parent company, International Textile Group, still produces some denim in their remaining US facilities. It’s not the same as the hallowed selvedge from the vintage shuttle looms, but it’s American-woven fabric nonetheless.

Then there’s the last true giant of American production: Texas Jeans. Operating out of Asheville, North Carolina since 1977, they produce approximately 2,000 pairs per week—all cut, sewn, and finished domestically. Their aesthetic isn’t exactly fashion-forward (think classic straight cuts that wouldn’t look out of place on a construction site), but their commitment to American manufacturing is unwavering. I spoke with their production manager, Dave, who’s been with the company for 31 years. “We’ve had opportunities to move offshore,” he told me, leaning against a cutting table the size of my apartment. “Turned ’em all down. That’s not who we are.”

The mid-sized players are where things get interesting. Brands like Round House, operating continuously since 1903 in Shawnee, Oklahoma, represent an unbroken lineage of American workwear. Their factory—which I visited on a blisteringly hot day last summer—looks practically unchanged from photos taken in the 1950s, right down to the wooden floors polished by decades of work boots. “We never left,” James, their fifth-generation owner told me, “because we never saw a reason to chase profit at the expense of our community.”

Meanwhile, All American Clothing Co. in Ohio has built their entire brand identity around domestic manufacturing, sourcing their denim from the remaining American mills and making every pair in their Arcanum facility. Their jeans use a tracking number system that lets you see exactly which American workers helped create your pants—a level of transparency that feels almost radical in today’s global supply chain.

But it’s the new wave of American denim brands that really gets me excited. These are the idealists, the craftspeople, and yes, sometimes the slightly insane perfectionists who are reimagining what American-made can mean in the 21st century.

Take Detroit Denim, founded in 2010 amid the city’s economic collapse. When I visited their workshop in an old stove factory, founder Eric Yelsma walked me through their process, which combines industrial sewing machines with hand details most companies abandoned decades ago. “We’re not trying to compete with jeans that cost a tenth of what ours do,” he explained while hand-hammering a rivet. “We’re trying to create something that couldn’t exist any other way.” Each pair passes through the hands of eight different craftspeople—all Detroit residents, many hired through local workforce development programs specifically created to rebuild manufacturing skills in the community.

Over in Los Angeles, Freenote Cloth operates one of the few remaining full-scale denim operations in what was once America’s jeans-making capital. Their sewing floor employs techniques virtually identical to those used by Levi’s in the 1960s, down to the chain-stitched hems and hidden selvedge details. “We’re preserving craft knowledge that nearly disappeared,” co-founder Matt Brodrick told me while showing me their collection of vintage Union Special machines. “These skills used to employ thousands of Angelenos. Now there’s maybe a hundred people left who know how to operate these machines properly.”

Perhaps my favorite discovery was Darkas Denim in White Bird, Idaho—possibly the most remote jean maker in America. Founded by former Levi’s pattern maker Daniel Marcellus, who left the corporate world to create an almost obsessively perfectionist version of American jeans, Darkas produces fewer than 500 pairs annually in a converted barn. When I asked why he chose such a remote location, Daniel laughed. “Land was cheap, and nobody bothers me while I’m working.” Each pair takes him approximately 11 hours to complete, using denims from the small-batch American mills trying to fill the void left by Cone’s closure.

Speaking of those mills—they’re another essential part of this story. While Cone Mills’ White Oak plant may be gone, smaller operations have emerged to continue the tradition of American-woven denim. Vidalia Mills in Louisiana has installed some of the original Draper X3 looms from White Oak, continuing to produce selvedge denim on American soil. In Maine, Maine Denim has converted part of an old paper mill to produce small-batch fabrics with locally sourced cotton. The scale is nothing like the industry’s heyday, but the quality and attention to detail are unmatched.

The hard truth, though, is that American-made jeans simply cannot compete on price with imported alternatives. The math is brutal and unavoidable. While overseas factories can produce jeans for as little as $5 in labor costs, American production starts around $35-50 per pair just in labor. Add in the higher cost of American fabric, complying with U.S. environmental and labor regulations (all good things, mind you), and the economics become challenging.

This reality is reflected in the retail prices. Entry-level American-made jeans typically start around $150, with the small-batch artisanal brands easily reaching $300-400. For most consumers, that’s simply not competitive with the $40-70 imports that dominate mall shelves.

So why bother? Why do these brands persist in making jeans domestically when the numbers seem stacked against them?

Every maker I spoke with eventually circled back to the same core reasons: quality control, ethical production, and cultural heritage. Being close to their production means they can monitor every step, adjust quickly when problems arise, and maintain standards that would be difficult to ensure from thousands of miles away. The ethical component matters deeply—fair wages, safe working conditions, and environmental responsibility all ranked high in their priorities. And then there’s the preservation of a uniquely American craft tradition, something many of them spoke about with genuine emotion.

“I could make more money doing almost anything else,” Roy Slaper of Roy Denim told me in his one-man workshop in Oakland, where he makes each pair of jeans entirely by himself from start to finish. “But then who would keep this knowledge alive? Who would show that Americans can still make things with their hands?”

For consumers, the question becomes whether these values are worth the premium price. I’d argue they absolutely are, though I recognize my position comes with sizable privilege. I’m fortunate enough to be able to spend more on fewer, better things—a luxury not everyone can afford. But even approaching this from a pure value proposition, American-made jeans typically outlast their imported counterparts by years, not months, bringing the cost-per-wear down significantly.

My own oldest pair of American-made jeans—some Raleigh Denim workshoppers I bought eight years ago—have been repaired three times and still serve as my weekend go-tos. At about 400 wears and counting, they’ve amortized to roughly 60 cents per wear. The European fast-fashion jeans I foolishly bought last year? Blown out after 25 wears, making them actually more expensive in the long run despite their lower initial price.

There’s also something profoundly satisfying about wearing jeans made by people whose names you might actually know, in factories you could actually visit. It connects you to a production chain that’s become increasingly abstract for most consumer goods. When my Raleigh jeans developed a tear, I didn’t trash them—I sent them back to the workshop where Victor, their repair specialist, patched them with beautiful handwork that added character rather than detracting from them.

Is American-made denim a growth industry? Probably not in the conventional sense. Most of the makers I interviewed have deliberately chosen to stay small, focusing on quality over volume. But is it sustainable? Surprisingly, yes. Nearly every brand reported steady or growing demand, primarily from customers who prioritize quality, ethics, and a connection to how their clothes are made.

“We’re never going back to making millions of jeans in America,” Eric from Detroit Denim acknowledged. “But we don’t need to. We just need enough people who care about the story behind their pants to keep the craft alive.”

And that’s really what we’re talking about—the preservation of craft, of knowledge, of a particular way of making things that values durability and human skill. In a world increasingly dominated by algorithms and automation, there’s something rebellious and necessary about jeans still made by human hands on American soil, carrying forward techniques pioneered by Levi Strauss and Jacob Davis nearly 150 years ago.

As for me, I’m wearing a pair of American-made jeans as I write this—heavy 14oz selvedge from a small batch produced in Tennessee, sewn in a workshop in Kentucky. They weren’t cheap, but they’ll be with me for years, perhaps decades, getting better with each wear. In a disposable world, that’s something worth paying for. And every time I see that little selvedge line peeking out from my cuff, I’m reminded of that first pair I found by accident, and how they set me on a path to appreciating things made with care and built to last—a quintessentially American ideal worth preserving, one pair of jeans at a time.

I have a confession that would probably get my menswear card revoked if such a thing existed: my most expensive clothing purchase last year wasn’t a tailored suit or a handcrafted leather jacket – it was a ridiculously priced running shell from a Scandinavian athletic brand that cost more than my first car payment. My girlfriend nearly had an aneurysm when she saw the receipt. “It’s just a jacket you sweat in!” she protested, not unreasonably. Here’s the thing though – six months and roughly 500 miles later, it’s possibly the most justified splurge in my entire wardrobe. The damn thing performs exactly as promised through Chicago winter runs, New York spring downpours, and that one ill-advised trail excursion in Colorado where I nearly got hypothermia but my core remained perfectly temperature-regulated.

Athletic wear sits in this weird spot in the modern guy’s closet – simultaneously the most technical garments most of us own and also the pieces we subject to the absolute worst conditions. We expect them to wick sweat, regulate temperature, prevent chafing, and still look decent enough for a coffee run, all while literally throwing our bodies around in them and then stuffing them into gym bags to marinate until laundry day. And somehow, we’re still surprised when the $12.99 “performance” shirt from the discount store bin falls apart after three washes.

I’ve spent the last two years on what my editor half-jokingly calls “The Great Athletic Wear Investigation” – systematically testing premium sports brands against their budget competitors to answer the question: which expensive athletic stuff is actually worth the money, and which is just clever marketing wrapped in moisture-wicking polyester?

The testing protocol was simple but brutal. Each piece got worn during actual workouts (none of that “lounging around watching Netflix in Lululemon” nonsense that’s become pandemic-era normal), washed according to instructions, and evaluated for durability, comfort, and whether it actually delivered on its performance claims. I’ve logged around 200 running miles, 50+ strength training sessions, an embarrassing number of yoga classes where I was the only guy in the room, and exactly one disastrous attempt at CrossFit that we shall never speak of again. My laundry hamper has seen things, awful things.

Let’s start with running gear, where the price-to-performance correlation is probably the most justified. After testing basically everything on the market, I’ve found that premium running shorts from brands like Tracksmith, Saysky, and the somewhat-obvious Lululemon genuinely outperform their cheaper counterparts in meaningful ways. The difference isn’t just marginal either – we’re talking fundamental improvements in how they move with your body, how they handle sweat, and how they hold up over time.

The Tracksmith Session shorts ($72) initially seemed insane compared to the $25 options from big box sporting goods stores, but after 100+ miles, the cheaper shorts had already developed that lovely permanent crotch sweat stain and relaxed elastic that turns a once-supportive waistband into a constant game of “will these fall down during this sprint interval?” Meanwhile, the Tracksmith shorts still look nearly new. The built-in liner – usually the first thing to deteriorate in running shorts – has maintained its support, and the moisture management is noticeably superior. When you break it down by cost-per-wear and performance benefits, the premium actually makes sense.

Similar story with high-end running jackets and shells. That Scandinavian splurge I mentioned? It’s from a brand called Saysky, and despite the heart-stopping price tag, it’s outperformed every other running jacket I’ve ever tested. The breathability-to-weather-protection ratio is almost witchcraft – somehow it keeps rain and wind out while still letting enough air circulate that you don’t feel like you’re running in a plastic bag. For serious runners in variable conditions, these premium shells aren’t a luxury; they’re practically a necessity if you actually want to maintain your training schedule year-round.

Where the value proposition gets murkier is in basic workout tees and tanks. After testing everything from $9.99 big box store specials to $78 “technical training tees” (yes, that’s a real price for what is essentially a t-shirt), the performance gap simply doesn’t justify the extreme premium in most cases. The sweet spot seems to be in the $30-40 range from brands like Rhone and Ten Thousand, where you get tangibly better fabric and construction than budget options without the absolutely bonkers markup of the highest-end stuff.

A notable exception: if you’re someone who gets exceptionally sweaty or has skin sensitivity issues, the premium materials in brands like Lululemon’s Metal Vent Tech line really do make a difference in preventing that post-workout skin irritation that cheaper synthetics can cause. My perpetually drenched friend Mike swears the $78 Metal Vent shirts are the only ones that don’t give him what he eloquently calls “synthetic fabric rash” after his particularly swampy weightlifting sessions. For him, it’s basically a medical expense at that point.

Let’s talk about the weird world of “athleisure” – that nebulous category of clothing technically designed for activity but primarily worn for comfort and style. This is where you’ll find the most egregious markups with the least performance justification. Those $128 joggers with a designer logo? Nine times out of ten, you’re paying for branding and fabrication that looks premium rather than actually performs better.

The exception here comes from brands that started as legitimate performance companies before expanding into the lifestyle space. Lululemon’s ABC pants and Commission shorts genuinely use technical fabrics and construction methods from their performance line, just adapted into more casual silhouettes. The four-way stretch, gussetted construction, and moisture-wicking properties actually do make for a more comfortable everyday pant, especially if you’re someone who moves between sedentary and active throughout your day.

In the training/gym category, there’s one brand that consistently justifies its premium positioning: Ten Thousand. Their Interval shorts ($68) have survived everything from heavy barbell training to muddy outdoor boot camps without a single popped seam or failed component. The thoughtful details – perfect pocket placement that doesn’t interfere with movements, liner options based on support preference, actual useful features rather than decorative nonsense – show they’ve been designed by people who actually work out seriously. Compared to the $25-30 gym shorts from big sporting goods chains that typically start falling apart within months, the cost-per-wear math actually works out in favor of the premium option.

The most surprising finding from my testing? Socks – yes, socks – might be where the premium/budget divide is most dramatic in terms of actual performance. After logging hundreds of miles in everything from bargain-bin six-packs to eye-wateringly expensive specialty running socks, the difference is undeniable. Brands like Feetures, Balega, and Swiftwick create products so superior to standard athletic socks that it’s almost unfair to compare them. The targeted compression, blister prevention, and durability aren’t just marginal improvements – they fundamentally change how comfortable your feet are during and after activity.

I’ve had $15 pairs of Balega running socks outlast six or seven pairs of cheaper alternatives, making them actually less expensive in the long run while delivering significantly better performance. When my non-runner friends balk at spending double-digit dollars on a single pair of socks, I’ve started asking them how much their feet are worth to them. Seems to put things in perspective.

Now let’s address the elephant in the performance-wear room: compression gear. After testing compression tights and tops from brands across the price spectrum, I’ve found that the premium brands (2XU, especially) do deliver measurably better graduated compression – meaning they actually apply different pressure levels across different parts of your body, rather than just being really tight spandex. For serious athletes doing intense training or requiring maximum recovery support, this technical difference matters. For the average gym-goer doing a standard workout? Probably not enough to justify the price gap.

As for those altitude training/oxygen restriction/body-heat-maximizing gimmick garments that pop up with outrageous claims and equally outrageous price tags? Save your money. I’ve tested several, and the only thing they reliably restrict is your bank account.

The most underrated premium athletic purchase might be cold-weather base layers. After testing essentially every major brand from bargain to boutique, the performance gap between budget synthetics and premium options from brands like Icebreaker, Smartwool and Tracksmith becomes dramatically apparent once the temperature drops below freezing. The difference in warmth-to-weight ratio, moisture management, and – let’s just say it – stink prevention justifies the investment if you’re serious about outdoor winter training.

One category where premium prices are almost never justified? Anything sold as “golf lifestyle” that isn’t actually used on a golf course. The markup on these items is astronomical compared to their actual performance characteristics. You’re basically paying country club membership fees built into the cost of a polo shirt.

My most unexpected discovery throughout this extended experiment has been how the warranty and repair policies of premium brands can actually make them better value propositions in the long run. When my Rhone shorts developed a weird seam issue after about a year of heavy use, they replaced them without question. When the zipper on my Lululemon jacket broke, they repaired it for free. That level of service is factored into those premium prices and can dramatically extend the useful life of your athletic gear.

After all this testing, my athletic drawer has become this strange hybrid – bargain basics sitting next to embarrassingly expensive specialized pieces, each earning its place based on actual performance rather than price tag or brand cachet. My running gear skews heavily premium because the functional benefits are undeniable for the mileage I put in. My general gym rotation includes more mid-tier pieces because the performance-to-price ratio makes more sense for activities where I’m not pushing environmental or endurance extremes.

The next time you’re experiencing sticker shock in the athletic department, ask yourself one question: is this something I do seriously enough, frequently enough, that incremental performance improvements would actually impact my experience? If you’re running five days a week in all weather conditions, that premium shell might be the most sensible wardrobe investment you could make. If you’re mostly just wearing workout clothes to look athletic while walking the dog, save your money for something else.

And those ridiculously expensive Scandinavian running shorts I mentioned at the beginning? Worth every penny for the simple fact that they’ve survived more than 100 washes without deteriorating, while I’ve bought and discarded at least six pairs of budget alternatives in the same timeframe. The math doesn’t lie, even when the initial price tag makes you sweat more than the workout itself.

The first time I really understood the value of American manufacturing was during a freezing January afternoon in Red Wing, Minnesota. I was standing in the middle of the Red Wing Shoes factory, watching a leatherworker hand-stitch a pair of Iron Ranger boots with the kind of focus usually reserved for brain surgery. The guy—Jim, according to his worn name patch—had been doing this particular job for 31 years. When I asked him about retirement, he just laughed and said, “What would I do with myself? Garden? I’m a bootmaker.”

Jim’s callused hands moved with the fluid precision that only comes from decades of repetition. He wasn’t just assembling a product; he was practicing a craft that had been refined over generations. The boots he was working on would sell for around $350—not cheap by any standard, but suddenly seeming like an absolute bargain considering the skill and time being poured into them.

That visit changed how I thought about the clothes and shoes I buy. Not in some abstract, jingoistic “buy American” bumper-sticker way, but in a concrete understanding of what we’re really talking about when we discuss domestic manufacturing. We’re talking about Jim and the 600+ other people employed in that factory. We’re talking about a small Minnesota city where manufacturing jobs still provide solid middle-class livelihoods. We’re talking about skills being preserved rather than lost to time.

I’ve spent the last decade visiting American factories whenever I can talk a brand into letting me tour their facilities. I’ve seen third-generation shirt makers in North Carolina, denim weavers in San Francisco, leather tanners in Chicago, and necktie makers in New York City. Each visit reinforces what I learned that day in Red Wing: American manufacturing isn’t just about a label or a point of pride—it’s about communities, craft, and a way of life that’s increasingly rare in our disposable economy.

Look, I’m not here to guilt-trip anyone. My own closet isn’t 100% American-made. I’ve got Italian shoes, Scottish sweaters, and yes, plenty of items from brands that manufacture overseas. But I’ve come to believe that intentionally supporting domestic makers whenever possible is one of the most meaningful ways we can vote with our dollars. It’s not about blind patriotism—it’s about preserving craft, supporting decent jobs, and honestly, getting some damn fine products in the process.

So let me walk you through the American brands that I believe are truly worth your hard-earned money—not just because they slap a flag on their products, but because they’re making genuinely excellent stuff while supporting local economies.

Let’s start with Alden. Based in Middleborough, Massachusetts, they’ve been making some of the finest men’s shoes in America since 1884. I own three pairs of Aldens—a shell cordovan plain-toe blucher that’s developed a patina like fine furniture, a suede chukka boot that’s molded to my foot like a second skin, and a newer pair of loafers that I’m breaking in. They aren’t cheap (most styles run $550-$750), but they’re the kind of shoes you’ll resole for decades rather than replace.

I once spent a day at the Alden factory, watching craftspeople perform the 130+ steps it takes to make a single pair of shoes. Many of the workers I met had been there for twenty-plus years, and several told me they were the second or third generation of their family to work for the company. When I asked the factory manager what made American shoemaking different, he didn’t hesitate: “We’re not trying to make the most shoes. We’re trying to make the best shoes.” That philosophy shows in every stitch.

Speaking of stitches, let’s talk about Gitman Bros. Their shirt factory in Ashland, Pennsylvania, is a master class in precision. Watching their seamstresses work is like witnessing a high-speed ballet—fingers guiding fabric through machines with millimeter accuracy, executing collar attachments and button alignments that would have taken me hours to complete (badly). Many of their employees have been with the company for decades, and that institutional knowledge is evident in the finished product.

A Gitman Oxford shirt costs around $165-$195 depending on the fabric. That’s three or four times what you’d pay for a mass-market shirt from a mall brand. But after wearing both, I can tell you the Gitman will still look good after 50 washings when the cheaper option has long since warped, faded, or simply fallen apart. Their attention to details most customers will never consciously notice—single-needle stitching, matched patterns at the seams, reinforced gussets—creates shirts that actually improve with age.

Denim is another category where American manufacturing truly shines. Brands like Raleigh Denim in North Carolina are creating jeans that rival anything coming out of Japan’s revered denim scene. Husband-and-wife team Victor and Sarah Lytvinenko started Raleigh in 2007, and they’ve built it into a beacon of American craftsmanship. They use vintage machines (including some rescued from factories that were closing), employ local talent, and create jeans that develop personality over years of wear.

I bought my first pair of Raleigh jeans six years ago and have since added two more to the rotation. At $295, they’re an investment, but they’ve outlasted multiple pairs of cheaper jeans, aging gracefully rather than simply wearing out. The fabric comes from Cone Mills White Oak—America’s last selvedge denim plant, which sadly closed in 2017 (Raleigh smartly bought up a significant stockpile of their denim before the closure).

On a visit to their workshop, Victor showed me how they map every pair of jeans, planning the fade patterns based on the specific characteristics of each denim lot. “We’re not just making jeans,” he told me. “We’re making the blank canvas for the next decade of someone’s life.” It sounds pretentious until you’ve worn a pair long enough to see your own story written into the fades and creases.

For knitwear, I’ve become a huge advocate of Hackwith Design House in Minnesota. Founded by Lisa Hackwith in 2010, they’ve built a production model focused on minimal waste, fair labor practices, and made-to-order garments that reduce overstock. Their heavyweight cotton sweaters have become a winter staple for me—substantial enough to replace a light jacket but refined enough to wear to dinner.

I actually discovered them when my girlfriend bought one of their dresses and wouldn’t stop talking about the quality. After visiting their studio and watching how they cut and sew each garment to order, I understand the enthusiasm. In an industry where overproduction and waste are endemic, their approach feels revolutionary. The price point (typically $175-$250 for sweaters) reflects the Minneapolis-based production and small-batch approach.

Then there’s Filson, the Seattle-based brand that’s been outfitting loggers, miners, and outdoorsmen since 1897. While they’ve become something of a fashion statement in urban environments, their core products remain true to their heritage—virtually bombproof bags, jackets that shrug off decades of abuse, and shirts that your grandchildren might someday fight over inheriting.

I’ve had my Filson briefcase for eleven years now. It’s accompanied me to fashion weeks across three continents, been stuffed into countless overhead bins, and served as an impromptu seat during more than one delayed train journey. The twill has softened and developed a patina that tells the story of those years. The British guy sitting next to me at a show in London once offered to buy it off my back for twice what I paid for it. (I declined.) At around $350, it wasn’t cheap, but amortized over more than a decade of daily use, it’s been one of my smarter investments.

For tailored clothing, I’ve developed an appreciation for Southwick, which has been making suits in Massachusetts since 1929. Now owned by Brooks Brothers, they maintain a factory in Haverhill that employs highly skilled workers producing garments with old-world attention to detail. Their natural-shouldered jackets—particularly in their signature Douglas model—have a distinctly American ease about them.

My navy Southwick blazer has been a workhouse of my wardrobe for five years and counting. The half-canvas construction has molded to my body over time, and the fabric has maintained its shape and color despite regular wear. At around $900-$1,200 for a suit (depending on fabric), they’re competing with entry-level offerings from Italian and English makers, but the quality stands up to the comparison.

Of course, American manufacturing isn’t limited to heritage brands or traditional product categories. Younger companies like Taylor Stitch in San Francisco are bringing domestic production to more contemporary designs. Their responsibly-built garments combine classic American workwear influences with modern fits and fabrications. Their Heavy Bag T-shirts, made from recycled cotton and recycled polyester in Los Angeles, have become my go-to casual shirts—substantial enough to wear alone, versatile enough to layer.

What makes me particularly optimistic about brands like Taylor Stitch is their commitment to transparency. They openly discuss their manufacturing partners, material choices, and production challenges. When they can’t make something domestically at a price point that makes sense, they say so rather than hiding behind vague marketing language.

Even footwear startups have found ways to manufacture domestically despite the significant barriers to entry. Portland’s Danner continues to make some of the best hiking boots in the world right in Oregon. Their Mountain Light hikers—featured in the film “Wild” and beloved by actual hikers and fashion folks alike—represent American craftsmanship at its finest. I’ve had mine resoled twice, and they’re still going strong.

This brings me to an important point: supporting American-made isn’t just about the initial purchase—it’s about the repairability and longevity of these products. Most domestic manufacturers stand behind their goods with repair services that extend their lifespan dramatically. Red Wing will resole your boots. Filson will repair your bag. Alden can essentially rebuild your shoes from the inside out.

This repair infrastructure represents another layer of meaningful employment and skill preservation. The guys at my local Red Wing store who evaluate boots for reconditioning are preserving knowledge that would otherwise disappear. When you buy from these brands, you’re supporting not just the initial manufacturing but this entire ecosystem of maintenance and repair.

Now, there’s an uncomfortable reality we need to address: American-made goods generally cost more than their imported counterparts. The reasons are straightforward: higher labor costs, stricter environmental regulations, shorter supply chains with fewer economies of scale. That higher price point makes these goods inaccessible to many Americans, creating a paradoxical situation where domestic manufacturing becomes a luxury rather than the standard.

I don’t have a perfect solution for this tension. What I do know is that changing our relationship with consumption—buying fewer, better things and maintaining them—can make higher-quality goods more accessible over time. The math sometimes works out: three $25 shirts that last one season each, or one $75 American-made shirt that lasts for years? The initial outlay is the same, but the value proposition changes dramatically.

For me, the most compelling reason to buy American-made transcends the physical product entirely. When I visit these factories and meet the people behind the products, I’m struck by the pride they take in their work. These aren’t just jobs; they’re careers and identities. The patternmaker at Gitman who’s been perfecting shirt proportions for 30 years. The leather cutter at Alden who can evaluate a hide with a glance and a touch. The sewing machine operator at Filson who signs her name on bags she constructs.

These skilled trades represent something valuable in our increasingly digital, abstract economy—the tangible satisfaction of making real things with your hands. Supporting these manufacturers means voting for an economy where such work remains viable, where craftsmanship still matters, where things are built to last rather than to be quickly replaced.

Is buying American-made going to single-handedly revitalize domestic manufacturing? Of course not. The economic forces that shifted production overseas over the past half-century are complex and powerful. But consumer choices do matter. Every Alden shoe purchase helps keep their factory running. Every Raleigh jean sold makes their business model more sustainable.

I’ve seen the impact firsthand. Several American factories I’ve visited have actually expanded operations in recent years, adding employees and equipment as demand for their products has grown. Others have managed to stay afloat through challenging economic periods because a core group of loyal customers values what they do.

So next time you’re considering a clothing purchase, take a moment to look into where and how it was made. Not every item in your closet needs to be American-made, but incorporating some domestically produced pieces connects you to this broader tradition of quality and craft. You’re not just buying a shirt or a pair of boots; you’re buying into an idea of how things can be made, how workers can be treated, and how long goods should last.

That Iron Ranger boot I watched Jim working on in Red Wing? I bought a pair that day. Seven years later, they’ve been resoled once and developed a patina that tells the story of countless city miles, hiking trips, and winter storms. They weren’t cheap, but divided by the years of service they’ve provided, they’ve been one of the best values in my wardrobe. And every time I lace them up, I think about Jim and his three decades of craftsmanship, about the factory that employs hundreds of his neighbors, and about the small Minnesota town where American manufacturing isn’t just a marketing slogan but a living tradition.

The boots will probably outlast me. And in a world of disposable everything, there’s something profoundly satisfying about that.

The first time I ever walked into a thrift store with the intent to actually buy something, I was twenty-two and broke as hell. My first “real” job interview was the next morning, and I needed a suit that wouldn’t make me look like I was wearing a borrowed costume. My budget was somewhere between laughable and nonexistent, which is how I found myself in a Goodwill on Chicago’s North Side at 6:45 PM on a Tuesday, digging through racks of discarded formal wear that smelled vaguely of mothballs and old cologne.

I must have tried on fifteen different jackets before I found it—a charcoal gray Brooks Brothers in what appeared to be nearly perfect condition. The pants were nowhere to be found, but the jacket fit like it had been made for me. Twenty-two bucks. I paired it with some dark navy trousers I already owned (a rookie mistake, but better than the alternative), polished my one pair of decent shoes, and somehow landed the job despite my mixed-up suit. The interviewer—a guy named Richard with immaculately tailored everything—actually complimented the jacket. “Brooks Brothers, right? Older model, maybe ’90s? Good find.”

I nearly choked on my water. That was the day I realized two things: people notice quality even if they can’t articulate why, and thrift stores are gold mines if you know what you’re doing.

Fast forward about a decade, and my apartment now contains more secondhand designer pieces than I’d care to admit to my financial advisor. That twenty-two dollar blazer kicked off what my ex-girlfriend called “an unhealthy obsession” and what I prefer to think of as “strategic wardrobe building.” I’ve since discovered that thrift store shopping isn’t just about saving money—though god knows I’ve done plenty of that—it’s about finding pieces with character, quality, and history that you literally cannot buy new anymore.

Last month, I found a Polo Ralph Lauren tweed sportcoat from the early ’90s when they were still making them with full canvassing and natural shoulders in the USA. The price? Thirty-five bucks. The same jacket new today would run you $900 and wouldn’t be half the quality. My best friend Trevor refuses to go thrifting with me anymore because, according to him, “watching you fondle old jackets and mutter about stitching for three hours isn’t my idea of a Saturday well spent.” His loss.

Look, I get it. Thrift shopping isn’t for everyone. There’s a certain… let’s call it an aroma that permeates most secondhand stores. The lighting is usually terrible. You’ll have to sort through endless racks of truly hideous clothing. And yeah, occasionally you’ll run into someone who’s having an animated conversation with an invisible friend by the housewares section. But for me, the hunt is half the fun. It’s like a treasure hunt where X marks the spot of a perfectly broken-in Alden loafer or a Brioni tie for less than you’d pay for lunch.

So, for those of you brave enough to dive into the world of high-end thrifting, here’s what I’ve learned from years of hunting down designer pieces that rich guys got tired of:

First—and this is non-negotiable—you need to know your labels. Not just the obvious ones like Ralph Lauren and Brooks Brothers, but the niche players too. Spend some time educating yourself about what the inside of a Zegna tag looks like versus a Zara knockoff. Learn to spot the difference between Alden and Aldo shoes at a glance. This research will save you from bringing home expensive-looking garbage.

One rainy Thursday, I found what I thought was a Burberry trench coat for $40. I was so excited I didn’t bother with my usual inspection ritual. Got it home, went to clean out the pockets and found a tag I’d missed—”Burberri” with an “i.” Couldn’t return it because I’d already removed the thrift store tags. My roommate Marcus still calls it my “Burberri adventure” and no, it wasn’t funny the first fifty times either.

Second, develop a circuit and hit it regularly. My personal rotation includes three Goodwills, two church thrift shops, a consignment store that doesn’t understand how to price menswear, and a Salvation Army near a wealthy suburb where finance guys dump last season’s impulse purchases. I visit at least one spot per week, usually on weekday evenings when they’re less crowded. Timing matters—ask the staff when they put out new merchandise and plan accordingly.

It was during one of these regular sweeps that I found my white whale: a perfectly preserved 1960s Oxxford suit in a charcoal sharkskin wool that makes modern suits look like they’re made from paper towels. The full story involves me sprinting across a parking lot to beat another shopper to the rack, but some details are better left untold. Just know I regret nothing.

Third—and this separates the amateurs from the pros—always, always check wealthy neighborhoods. The donation drop-offs near Gold Coast or Lincoln Park in Chicago, Upper East Side in New York, or Beverly Hills in LA? Absolute gold mines. Rich people clean out their closets too, and they’re a hell of a lot less likely to wear things until they fall apart. Some of my best finds have come from stores where bored housewives drop off their husbands’ barely-worn clothing because they “needed closet space for the new collection.”

My buddy Eric once found three Charvet dress shirts with the dry cleaning tags still attached at a Goodwill in Winnetka. Retail price would’ve been around $400 each. He paid $7.99 per shirt and looked liked he’d won the lottery the entire rest of the day.

Fourth, make friends with the staff. I’m on a first-name basis with Diane who runs the men’s section at my favorite Goodwill. She knows what I like and sometimes sets things aside. In exchange, I bring her coffee and don’t haggle on prices that are already ridiculous. This relationship has paid dividends—like the time she called me about a donation that had just come in: three pairs of Allen Edmonds, barely worn, in my exact size. The previous owner had died (a bit morbid, I know), and his son had dropped off his entire closet. I still wear those shoes at least weekly and silently thank both Diane and the unknown original owner.

Fifth, know when to splurge and when to walk away. That cashmere Loro Piana sweater with a tiny moth hole? Probably worth the $25 if you know a good tailor who can repair it invisibly. That Gucci shirt from 2003 with the massive logos all over it? Leave it for some fashion student’s ironic project. Buy quality, not labels, and certainly not trends that were questionable even when they were new.

I once left behind a genuine Versace silk shirt because it was a ’90s print so loud it would’ve made Elton John ask if I was feeling okay. My friend Marcus still hasn’t forgiven me—he’s convinced it would’ve been worth hundreds to the right vintage collector. Maybe he’s right, but I couldn’t in good conscience add it to my wardrobe, and I’m not in the business of reselling.

Sixth, learn basic alterations or make friends with a good tailor. Most of my thrifted pieces have been adjusted in some way. Sleeves shortened, waists taken in, buttons replaced. My tailor, Jun, has saved countless finds that were almost perfect. He charges me a bit less because I bring him regular business, and I occasionally bring him bottles of the Japanese whisky he likes. The cost of the item plus alterations is still usually about 10-20% of retail, and the result is clothing that fits better than anything you’d buy off the rack.

Case in point: I found a Cucinelli sport coat last year for $45. It needed the sleeves shortened and the waist taken in slightly—another $65 in alterations. So $110 all-in for a jacket that would have cost north of $3,000 new. And because the previous owner had already broken it in, it has a comfortable, lived-in quality that new clothing lacks.

Finally—and this is crucial—know what can’t be fixed. Shoulders on a suit jacket? Nearly impossible to alter well. Stains on silk? Forget about it. Heavy wear on shoe soles? Probably not worth resoling. Learn to spot these deal-breakers quickly so you don’t waste time falling in love with something that’s fundamentally flawed.

I made this mistake early on with a gorgeous pair of Crockett & Jones oxfords that had clearly been worn in the rain repeatedly without shoe trees. The leather was cracked in ways that no conditioner could resurrect. Sixty bucks wasted on shoes I couldn’t save. A painful lesson, but an effective one.

The real joy of thrift shopping isn’t just saving money—though finding a $2,000 blazer for less than the cost of two movie tickets never gets old. It’s about the stories. Every item has lived a life before it came to you. I have a Turnbull & Asser tuxedo shirt that still had the previous owner’s collar stays in it, monogrammed “ASW.” I sometimes wonder who ASW was, where he wore this shirt, what occasions it witnessed. There’s something almost poetic about giving these pieces a second life.

Not that I’m getting all sentimental about used clothing. But there’s a satisfaction in building a wardrobe of exceptional pieces that most people couldn’t afford at retail—not because you’re trying to front like you’re richer than you are, but because you’ve put in the time to learn what quality looks and feels like.

So next time you pass a thrift store and think “not for me,” maybe reconsider. That Goodwill in an unassuming strip mall might just have a piece of fashion history hanging on its racks, priced somewhere between a fancy coffee and a cheap dinner. And even if you walk out empty-handed, the education is free. Just don’t tell too many people about your favorite spots. I’m still mad at whoever wrote that viral TikTok about my church thrift store. Some treasures are better kept secret.

Last month I found myself in this pretentious menswear store in SoHo—you know the type, concrete floors, exactly three shirts on display, salespeople dressed like Victorian undertakers. I was there interviewing the founder for a feature, and he kept throwing around the phrase “American heritage” like he was personally responsible for preserving national treasures. At one point, he actually said with a straight face: “Our $395 selvedge denim is inspired by the authentic spirit of the American frontier.” I nearly choked on my complimentary sparkling water. The guy was from Connecticut and had launched his brand in 2018.

Don’t get me wrong—I love American style classics as much as the next menswear nerd. Hell, probably more, considering I have an entire storage unit filled with vintage workwear that my ex-girlfriend used to call “the museum of things that smell like other people’s grandpas.” But there’s something that drives me absolutely nuts about how the term “American classic” gets thrown around these days. It’s become less about historical accuracy and more about creating convenient myths that sell $300 T-shirts.

Here’s the thing about true American style classics—they weren’t created to be classics. They were created to solve specific problems, usually by people who were too busy working to care about looking “authentic.” Take the Levi’s 501. We now treat it like some sacred text of American design, but it started as literal work clothes for miners and ranch hands. They weren’t trying to create an icon; they were trying to make pants that wouldn’t fall apart when you were, you know, mining for gold. Function first, fashion nowhere on the priority list.

My grandfather worked at a steel mill in Pennsylvania for 38 years. I once showed him an “authentic reproduction work shirt” I’d bought for an embarrassing amount of money, and he laughed until he started coughing. “We would’ve set fire to something that stiff,” he said. “Couldn’t move your arms properly.” Heritage brands love to talk about the “honest workers” who inspired their collections, but actual working people prioritized comfort and durability over some romantic notion of rugged authenticity.

The marketing mythology around American classics gets especially weird when brands start inventing histories that never existed. I was at a trade show in Las Vegas last year when a brand rep cornered me to tell me about their “historically accurate reproduction” of a military jacket from 1943. I happen to collect vintage military gear (I know, I’m a walking cliché), so I asked some specific questions about the original specs. The guy couldn’t answer any of them. Later, I discovered the design they were “reproducing” never actually existed—they’d combined elements from several different eras and invented a backstory. That’s not heritage; that’s historical fan fiction.

But here’s where it gets complicated. Some American classics genuinely deserve their status—they really did change how people dressed and have remained relevant for decades. The white t-shirt, for example. Originally an undergarment for Navy sailors around 1913, it emerged as outerwear during WWII, got the James Dean treatment in the 50s, and has never left the cultural conversation. Or the aviator sunglasses, which were literally designed for pilots in the 1930s but still look great today. These are the real deal—designs that have proven their staying power across generations without much modification.

My buddy Marcus makes an important distinction that I’ve adopted: “Is it a classic because it’s good, or is it ‘good’ because someone says it’s a classic?” Lots of stuff falls into that second category. The penny loafer gets talked about as this eternal American staple, but it’s been in and out of fashion dozens of times. Same with the button-down oxford shirt. These aren’t bad items—they’re great, actually—but their “classic” status has been carefully managed and marketed over decades.

The marketing of American classics often relies on selective history. Brands love to talk about how their khakis were worn by WWII officers but conveniently forget that the design originated as colonial British military uniforms in India. Or they’ll wax poetic about the rugged individualism of the cowboy boot while glossing over its mixed Spanish, Mexican, and Native American influences. American style is actually at its best when it’s honest about being a melting pot of influences, just like the country itself.

I ran into this friction firsthand when researching an article about the history of the leather jacket. A major American brand had built their entire marketing story around being “the original,” with ads suggesting their founder basically invented the concept in the 1920s. When I dug into actual historical records and vintage examples, it became clear that leather jackets had been evolving across multiple countries simultaneously, with key innovations coming from military contractors, motorcycle companies, and European designers. When I included this in my article, the brand pulled their advertising from our website for three months. Apparently, historical accuracy was less important than their founding myth.

What’s especially funny is how many “all-American classics” aren’t remotely American in origin. The desert boot? British design inspired by shoes worn in Egypt. The field jacket? Variations exist from military traditions worldwide. Denim itself? The fabric originated in Nîmes, France (hence “de Nîmes” becoming “denim”). But marketing departments can’t sell “multinational design traditions thoughtfully adapted for American use”—not as catchy as “BORN IN THE USA!” plastered over a filtered image of some model pretending to chop wood.

The price inflation that comes with this mythmaking is what really gets under my skin. Last week I watched a guy in Brooklyn pay $985 for a “heritage-quality” reproduction of a canvas work jacket that I found the actual 1950s version of at a thrift store in Ohio for $15. The reproduction was beautiful, sure—perfect stitching, historically accurate pattern, artisanal whatever. But paying luxury car money for a simulated working-class garment feels… I don’t know, weird? Maybe I’m overthinking it.

Then again, I own a painfully expensive reproduction of a World War II flight jacket, so maybe I’m part of the problem. I justified it by telling myself it was better constructed than anything I could find vintage in my size. That might be true, but I also just wanted it, which is probably the more honest answer. We all have our hypocrisies, especially in how we approach style. I’ve made peace with mine, mostly.

My friend David, who works as a vintage dealer in Chicago, has a theory I find compelling. He believes the obsession with American classics actually intensified as American manufacturing declined. “It’s nostalgia for something we’re actively destroying,” he told me over beers last time I was in town. “We shut down the factories, moved production overseas, and then fetishize the products those factories used to make.” There’s something perverse about a $400 “American heritage workwear” shirt made in a factory with questionable labor practices on another continent. But that’s the reality behind a lot of what gets marketed as classic Americana.

Of course, there are exceptions—brands that are genuinely committed to both historical accuracy and ethical modern production. They tend to be smaller, more specialized, and refreshingly straightforward about what they’re doing. I visited a workshop in Portland last year where they’re making bags using machines and techniques from the 1940s. No fake backstory, no sepia-toned marketing—just people who love traditional craftsmanship keeping it alive. That feels different from the corporate heritage cosplay that dominates the market.

It’s easy to become cynical about all this, but I try to remember that every generation reinvents tradition in its own image. The “authentic” Americana workwear obsessives of the 2010s weren’t actually more authentic than today’s reinterpretations. And the original makers weren’t thinking about authenticity at all—they were just solving problems with the technology and materials available to them at the time. Maybe authenticity is a weird standard to apply to clothing in the first place.

I had dinner with my dad last time I was home in Chicago, and he pointed to my jacket—a reproduction of a 1950s style—and asked if it was vintage. When I explained it was new but based on an old design, he looked genuinely confused. “So it’s a costume?” he asked. I started to explain about heritage design and historical references, but halfway through my explanation, I realized I sounded ridiculous. From his perspective, there was vintage clothing (old stuff) and modern clothing (new stuff). This middle category of new things pretending to be old things didn’t make sense to him. And maybe he had a point.

There’s a store in Manhattan that sells $300 reproductions of jerseys from Negro League baseball teams of the 1930s. The craftsmanship is impressive, and the designs are beautiful. But when I interviewed the founder for a piece last year, I asked how much of their profit goes to the families of the original players or to supporting causes related to the Negro Leagues’ history. There was an awkward pause followed by some corporate doublespeak about “raising awareness.” This is the dark side of the American classics industry—borrowing cultural equity without giving anything back.

So what’s the alternative? I’m not suggesting we can or should only wear actual vintage clothing (though that would certainly be better for the planet). And I do believe there’s value in keeping traditional designs and techniques alive. I guess I just wish there was more honesty in how these products are marketed. Don’t tell me your five-year-old brand is “authentic American heritage” when your founder worked at Goldman Sachs until 2018. Don’t charge heritage prices without heritage quality. And maybe acknowledge that American style, at its best, has always been about adaptation and evolution rather than preserving some mythical golden age.

The most genuinely “classic” American garment I own is probably my dad’s Carhartt chore coat from the 1980s. It’s beaten to hell, patched in three places, and the corduroy collar is worn smooth from four decades of wear. He never thought of it as a style statement—it was just the coat he wore to do yard work. But every time I visit home, I notice how young guys in his neighborhood are now wearing new versions of the exact same coat, carefully distressed to look like they’ve done a hard day’s work when they’ve actually just been to Starbucks. Dad finds this hilarious. “They’re paying to look like they can’t afford a new coat,” he says.

Maybe that’s what I find so funny about the whole “American classics” market. The original versions of these garments were usually designed to be affordable, practical options for people who needed durable clothes for hard living. Now we’ve transformed them into luxury goods, status symbols that signal how much you know about the history of clothes most people used to wear because they couldn’t afford anything fancier.

The irony is delicious, even as I participate in it myself. I’m not above the contradiction—I just think we should acknowledge it. There’s nothing wrong with appreciating well-designed classics or even paying for quality reproductions. Where it gets weird is when we start inventing mythologies to justify our purchases or pretending that buying expensive versions of workwear somehow connects us to an authenticity we’re otherwise missing.

The next time a brand tries to sell you on their authentic American heritage, maybe ask a few questions. When were they founded? Where are their products actually made? What problem was the original design trying to solve? And most importantly, does the product stand on its own merits without the mythology? The true classics always do—no origin story required.