I was killing some time (i.e. procrastinating work I should’ve been doing) at a coffee shop last Tuesday, sitting on the Lincoln Park patio people watching. I’ve always found people watching to be a fascinating pastime–meandering about with no real purpose except to observe others going about their lives. I sipped on my second coffee (I regret nothing) when I suddenly noticed something.
Within the span of twenty minutes I saw at least six unique males (stylistically speaking) walk past me. Not one of them dressed like the next guy. Each outfit gave off totally different vibes about how each guy perceived men should dress.
There were the two dudes in identical Patagonia quarter-zips jogging past each other (literally the same fleece, same color). Followed by some age-old businessman sporting a full Brooks Brothers pressed navy suit look.
Right behind him was ubrawhodedenim guy (we’ll get to who “we” are later) trailed by one of the coffee shop’s baristas who looked like he knew an excessive amount about Japanese workwear.
The more I thought about it, the more I realized that male style was vast and expansive. There were so many different styles, so many different camps that men fell into when it came to clothing. Different groups that dressed certain ways to signal certain things about themselves.
And the crazy part is most men probably don’t even realize they’re doing it. Over the past few weeks I’ve put some serious thought into what these groups are. Some of you will probably find familiarity in one or more of these groups.
Some might feel attacked. Truth is, all of these groups exist. You just have to know where to look.
Group #1: The Traditional Guys We’ll start with the ones whose sense of style hasn’t changed since they were young adults. Let’s call them…the Corporates. My dad is one of these guys.
He’s worn Hart Schaffner Marx suits for as long as I can remember. Seriously, he wears the same three suits, rotated and replaced as necessary when they wear down. White, navy, charcoal button ups.
Conservative ties. Cap toe shoes he shines on Sunday nights while watching 60 Minutes. I noticed him out of the corner of my eye when he was walking his dog last weekend and he was still wearing the exact same style of suit as I remember from twenty years ago.
This is a dude that sends a clear message with his clothing. He goes to work, he works hard, and he respects the dress code. These guys shop Brooks Brothers, J.
Press, maybe JOS A. BANK if they’re feeling economical. When it comes to weekend clothes?
Khakis and a blazer. Boom, that’s it. I interned at a law firm my summer out of college and you could spot the JBlass and Brooks Brothers across a parking lot.
Not joking. When I dared remark to my dad that he should try a more modern slim fit he eyed me as if I’d asked him to wear polyester leisure suits to court. Group #2: The Cool Guys Ah yes, the Coastal Creative.
You’ll find these guys hanging out in Williamsburg or Silverlake wearing easy jeans and some sort of fleece-lined boxy overshirt that costs more than my monthly rent. Oversized everything, tucked into high wasted jeans that aren’t quite skinny but aren’t yet baggy either. Color palette consists of navy, olive, oatmeal, black.
If they saw a hot pink shirt they would rip their eyes out. JBounds, JRooters, JWhite…. Union is their church.
Anyway you know these guys. They get their clothes at APC and Folk and spend way too much time looking at the “New Arrivals” section on END Clothing. I’m partly in this tribe.
Ask me about my favorite Japanese denim brand and I’ll give you a novella. Ask me how to dress for anything other than frigid NY winters and I’ll draw a blank. The other day I was cleaning out my closet to move and realized I own 17 navy blue shirts.
SEVENTEEN NAVY BLUE SHIRTS! They all look the same to everyone else but I can tell the subtle differences. Meanwhile my girlfriend laughs at me and says “ Dude you know you’re a cartoon character, right?” No….but I would look good in a sweater vest… Group #3: The Nerds Now we’re getting into my people.
The dudes that take wardrobe more seriously than most people’s careers. You know them, we know them. We call them…the Heritage Boys.
Vintage Levi’s aficionados. The guys whose idea of athletic clothing is a pair oflined targhee boots. Clyde but like a hundred times more specialized.
Heritage boys live and breathe clothing. Ask them where their jeans were manufactured and they’ll give you the history of that factory’s production for the past 75 years. Spend enough time with them and they’ll regale you with tales of Japanese denim mills so small you’ve probably never heard of them.
They shop Robert Geller, RRL, + Dead Stock. Unearth some vintage Eastless Coast EECs? SaDHoP they come home.
I was extremely into heritage when I was 24. My entire apartment was denim indigo and brown leather. Still owns the holey jeans I tried to slit up the outside seams with a pocket knife.
I spent an entire Saturday doing lunges around my apartment in order to break in a new pair of raw jeans. My upstairs neighbor called the police on me thinking I was either having sex and/or punching a pregnant woman. Never thought about my actions but hey, at least I got a nice fade.
These guys love authenticity and craft more than anything. They spend $300 on a reproduction 1947 football jacket and convince you it’s the best investment you’ll ever make. They can name drop union manufacture history and have favorite denim repair shops.
It’s kind of silly but also sort of amazing. Group #4: The Sweatpants Billions Ever notice how guys that workout actually look like they want to workout all the time? I’m serious–the_amount_of_times_I’ve_said_that_fit_guy some sort of athletic clothing seems normal enough but then you look closer.
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Lululemon ABC pants, quarter zip pullovers, technical sneakers that “tie” together their look when they’re just going to Starbucks. Skinny jeans replaced with jogging pants from the Gap. It’s a whole lifestyle these guys sell you.
And we bought it. They’ll tell you about the “details” and “technical aspects” of their clothes whether you care or not. I respect these guys.
I’m just not quite one of them. There’s something smart about wearing clothes that were literally designed to be awesome. Every one of my friends that dresses like this pulls off the look and actually looks like they could run a marathon at a moment’s notice.
Meanwhile I’m the asshole asking if we should Uber because “these shoes don’t really walk well.” They wear Patagonia underwear as pants and think its….normal? ? Group #5: The Y”cThank You for Your Continued Support”mens Oh streetwear, how do I love thee? Let me count the ways.
Graphic tees, sweatsuits, limited edition sneakers, jackets that cost more than my monthly car payment. Fitspo guys worship these people. Throw any sort of brand on them and they’ll wear it.
Always rotating through fresh drops because obviously these aren’t clothes…they’re “investments.” Unless HUF suddenly starts putting a bunch of ironic fuck-you’s on their shirts I’m probably never going to wholly be part of this tribe. But I love them. There’s something unique about guys that can style a snapback and joggers two dozen different ways.
Brand loyalty changes weekly but you can bet Supreme, Nike, and The Newest Mom+Pop collab will always be represented. Oh and did I mention they only wear graphic t shirts that say something? Long live Air Force Ones.
Group #6: The New Preps These guys took basic prep style and made it awesome again. They love their oxford shirts, loves their navy blazers and loafers. But they’re not afraid to wear a rugby shirt with some vintage military pants or switch up their penny loafers with old workwear instead of chinos.
Guys like Todd Snyder, Rich Williams, and Rowing Blazers spearhead this movement. Had the coolest conversation with a 22-year-old in Boston last summer. He was wearing his grandfather’s vintage Lacoste cardigan with loose fit jeans and loafers.
When I told him how great he looked he gave me a two+ minute history on how prep style became way more than just a preppy uniform. Thought about offering him my job. Group #7: The Minimalists If you want to bebasic bitch about it, these guys love their minimalist staples.
All black, gray, white and navy. Cozy, yet oddly not. Tailored but not formal.
Taught by(names that guys in NYC seem to know without fail) like COS, Uniqlo U, Japanese brands I can’t even pronounce. These guys make wearing almost all black not look like a funeral…but then again they could probably afford to bury me in COACH. I’ve dabbled in this trend more than I care to admit.
Going out becomes “too much effort” and I just want to crawl into myLiving.In… socks. But the problem is I spill coffee on myself constantly. Anything that isn’t dark blue or black ends up making me look like a human Rorschach test.
Group #8: Them Cowboys Alright guys. These are the ones we all wish we were. Whether they’re actually from Montana riding cattle or Brooklyn bartenders playing pretend, they dress the part.
Waxed jackets, flannels, leather boots, occassional western hat. Think:Filson, Barbour, Pendleton. Mixed in with some vintage randomos that have fake fox fur on them.
I spent way too much time with this photographer in Wyoming and marveled at how his waxed jacket had actual wax on it. From being outside. Not from him buying vest worn down in Vegas or something skeevy like that.
He could identify any bird we pointed at and build a fire in the rain. And I realized that my so called “rugged” apparel had never once gone camping. The interesting thing about all these groups is that I see pieces of myself, and clothes I wear, in each one.
I have Alden loafers sitting next to Nike Dunks in my closet. Custom suits that hang next to vintage military jackets. Who am I?
Take away my clothes and I’d probably have no idea. Does that sound depressing? It probably is.
But also it’s sort of freeing. We don’t have to conform to one style. We can wear whatever the hell we want that expresses who we are.
Or want to be. I was getting dressed for work the other day putting on a navy suit with a white oxford button up. Then for some reason I reached for my Jordans.
Six months ago I would’ve thought myself a hypocrite for pairing “corporate” clothes with streetwear. Now I just wore whatever the fuck I felt like and looked awesome doing it. So the moral of the story is wear what you want guys.
These are just groupings that I’ve noticed.
Personally identify with. Fall into and out of as your style evolves.
And heck, if you find yourself leaning hard into one category? Own it. Podcast about it.
Design clothes that fuel your dads cutting holes in his jeans so he can achieve that coveted washer/dryer fade. Just wear what makes you happy, and represents the best version of you. Or the version of you that you want to be.
Maybe both. P.s. Go people watch someday.
It’s awesome.
