So I’m sitting at this coffee place in Lincoln Park last Tuesday, supposed to be working on some campaign briefs but honestly just procrastinating hard and watching people walk by. You know how it is when you’re supposed to be productive but your brain decides it’s people-watching time instead? Anyway, I’m on my third coffee (probably a mistake but whatever) when I start noticing something weird. In like twenty minutes, I counted at least six completely different types of guys style-wise, and they all looked like they were following totally different rulebooks for how men are supposed to dress.
There’s these two tech dudes in matching Patagonia quarter-zips – I mean literally the same fleece in the same color, which is either really funny or really sad. Then this older guy walks by in a full Brooks Brothers situation, navy suit and everything, looking like he stepped out of 1987 but in a good way? Behind him there’s someone who’s clearly spent way too much time thinking about raw denim (I can spot us from a mile away), and then a barista who looked like he had strong opinions about Japanese workwear brands I’d never heard of.
It got me thinking about how men’s style isn’t really one thing at all. We’re basically all part of these different tribes, following different rules, signaling different stuff about who we are or want to be. And honestly, most of us probably don’t even realize we’re doing it.
I’ve been thinking about this for weeks now, and I think I’ve figured out the major groups. Some of these might sound familiar. Some might make you feel personally attacked. All of them are real, and they’re everywhere once you start looking.
The guys in suits who never change their minds about anything style-wise – I call them the Corporate Traditionalists. My dad is totally one of these. He’s been wearing the same Hart Schaffner Marx suits for literally my entire life, just replacing them when they fall apart. Navy, charcoal, white shirts, conservative ties, cap-toe shoes that he polishes every Sunday night while watching 60 Minutes. When I suggested he try a slimmer cut a few years ago, he looked at me like I’d suggested he start wearing leather pants to client meetings.
These guys aren’t boring though, they’re making a choice. Their style says “I’m here to work, I’m reliable, I respect tradition.” They shop at Brooks Brothers or J.Press, maybe Jos. A. Bank if they’re watching their budget. Weekend uniform is khakis and a blazer, end of discussion. I spent a summer at a law firm where this was basically mandatory, and these dudes could identify each other’s suit brands from across a parking lot. Wild.
Then you’ve got what I think of as the Coastal Creative types. These are the guys you see in Williamsburg or Silver Lake, wearing relaxed chinos and those boxy overshirts that somehow cost $300. Their whole thing is looking effortlessly cool while clearly putting a lot of effort into it. Color palette is navy, olive, oatmeal, black – anything more adventurous and they break out in hives, I think.
They shop at APC and Folk and probably spend way too much time on End Clothing looking at “New Arrivals.” I know because… well, I’m definitely mostly in this category, which is embarrassing but true. When I moved last year I realized I owned seventeen navy shirts. Seventeen! They all looked basically identical but in my mind they were completely different. My girlfriend just laughed and said “You know you’re a cartoon character, right?” She wasn’t wrong.
There’s something appealing about the subtle functionality of these clothes, but sometimes I wonder if I just look like I’m cosplaying as a Scandinavian architect. Which, honestly, maybe I am.
The Heritage guys are intense in the best way. These are the dudes who know more about vintage Levi’s stitching patterns than is probably healthy for any human being. Their closets are museums of workwear – selvedge denim, hefty flannels, boots that could survive nuclear war, military surplus jackets. They shop at RRL and Filson and Iron Heart, and they have a story about every single item they own. Where the cotton was grown, which factory made it, why the buttons are replicas of 1943 Navy issue.
I went through a serious Heritage phase around 24. My apartment looked like a denim factory exploded in it, all indigo and brown leather. I once spent an entire weekend doing lunges in new raw jeans trying to break them in properly. My upstairs neighbor thought I was either having very athletic sex or doing some weird workout routine. Neither was true – I was just trying to get perfect fade patterns on my Japanese selvedge. Not my most dignified period, looking back.
But these guys value authenticity and craftsmanship above everything else. They’ll pay $300 for a reproduction 1947 sweatshirt and explain why it’s actually an investment. They know union manufacturing history and can recommend specialty denim repair shops. It’s nerdy but kind of admirable.
The Athleisure people have basically won, let’s be honest. You see them everywhere now – upscale gyms, farmers markets, casual offices. Lululemon ABC pants, quarter-zip pullovers, technical sneakers for walking to Starbucks. Their whole wardrobe is performance fabric worn in completely non-performance settings, and they’ll tell you all about the technical features whether you ask or not.
I respect these guys even though I’ve never fully joined them. There’s something smart about building a wardrobe that prioritizes comfort and function. My Athleisure friends always look ready for anything while I’m the idiot asking if we can Uber because “these shoes aren’t really walking shoes.” They shop at Rhone and Vuori and justify the prices by claiming versatility – “These pants work for the office AND hiking!” – even though they’re mostly worn to sit in open floor plan offices.
Streetwear guys are probably the most interesting group right now. Their style revolves around graphic tees, hoodies, limited sneakers, and those statement jackets that cost more than my rent. Brand loyalty shifts constantly but Supreme, Nike, and whatever designer collaboration just dropped are always in the mix. They treat clothing like collectible art and cultural signaling combined.
What separates real Streetwear devotees from casual adopters is their depth of knowledge. They can recite designer histories and market values like baseball stats. Scoring a limited release isn’t just about having something cool – it’s about being recognized by others who understand its significance.
I’ve always been an appreciative outsider here. I respect the culture but don’t have the dedication for 6 AM lineups or the reflexes for online drops. I tried to buy collaboration sneakers once and got the “Sold Out” message literally 2.7 seconds after they went live. My computer might as well have laughed at me.
The Neo-Prep guys took traditional preppy style and made it interesting again. They’ve got the oxford shirts and navy blazers and loafers, but they’re mixing them in unexpected ways. Maybe pairing a rugby shirt with vintage military pants, or wearing penny loafers with workwear instead of khakis. Brands like Todd Snyder and Rowing Blazers define this space.
I met this 22-year-old in Boston last year wearing his grandfather’s vintage Lacoste cardigan with skate pants and loafers. When I complimented him, he gave me this amazing history of how prep style evolved from exclusionary uniform to something more democratic. I almost offered him my job. These guys are simultaneously respectful of tradition and subversive of it, which is a tricky balance to pull off.
Then there are the Minimalist Modernists with their beautifully cut basics in black, white, gray, and navy. Everything looks simple but costs as much as a laptop. COS, Uniqlo U, Japanese brands nobody can pronounce. Their outfits might seem boring until you get up close and notice the unusual fabric textures and perfect proportions.
I keep trying to join this tribe, especially during fashion weeks when I’m tired of thinking about what to wear. There’s something appealing about a uniform of perfect black trousers and white shirts. Then I remember I spill coffee on myself constantly and monochromatic dressing turns me into a walking Rorschach test.
The Rugged Individualists are everywhere from actual Montana ranches to Brooklyn bars pretending to be Montana ranches. Waxed jackets, flannel shirts, sturdy boots, occasional Western touches. Filson, Barbour, Pendleton, mixed with vintage pieces that suggest stories. They’re not just dressing for the life they have – they’re dressing for the life they want or want to be perceived as having.
I spent time with a photographer in Wyoming who embodied this perfectly. His waxed jacket was properly aged from actual outdoor use, not fake distressing. He could identify birds and start fires in rainstorms while looking like a heritage brand catalog. It made me realize my “rugged” clothes had seen more coffee shops than campfires, which was both embarrassing and motivating.
So which tribe are you? Honestly, if you’re like most guys, you’re probably borrowing from several. Maybe Corporate Traditionalist during the week but Streetwear on weekends. Perhaps Coastal Creative with Heritage tendencies when it gets cold.
That’s actually the cool part about men’s style right now – the boundaries are getting blurrier. We feel more freedom to experiment across categories, pulling elements that speak to different parts of who we are instead of pledging allegiance to one aesthetic.
My closet is evidence of every tribe I’ve described. Alden loafers next to Nike Dunks, custom suits hanging beside vintage military jackets. Each piece represents a different phase of my life, a different version of myself I was trying on or growing into. My girlfriend says it looks like five different people live in my apartment, and she’s not wrong.
But isn’t that what personal style should be about? Not rigidly following arbitrary rules, but using clothes to explore different parts of who you are or might become. The most stylish guys I know don’t fit neatly into any single category. They’ve figured out what works for them, what feels authentic, what tells their story.
The other day I was getting dressed for a client meeting and I put on a navy suit, white oxford shirt, and… wait for it… limited edition Jordan 1s. Six months ago I would’ve felt like a fraud mixing Corporate Traditionalist with Streetwear. Now I just felt like myself. Which I guess is the point.
So don’t worry too much about which tribe you belong to. The best style is personal style, even if that means being a lawyer with secret sneaker collections or a streetwear guy who can’t give up his grandfather’s tweed blazer. The contradictions are what make it interesting.
Next time you’re people-watching at a coffee shop (highly recommend, by the way), see if you can spot the different tribes. Then think about which elements from each one actually appeal to you, not because they’re “correct” but because they feel right. That’s where good style starts – with knowing yourself well enough to dress like it.
Jacob’s a Chicago marketing guy still figuring out his look one outfit at a time. His writing is honest, funny, and self-aware—sharing the hits, misses, and lessons learned while building an adult wardrobe that actually feels like him.
