There’s a moment that sticks with me from the first time I travelled to Charleston, SC eight years ago. Mid-July, mid-humidity – I was miserable wearing a cotton polo. And there I was watching Charleston men stroll around town wearing jackets.
Not lightweight tropical wool jackets, but STRUCTURED jackets. Jackets, in August, in Charleston, SC. Look, I was uncomfortable.
I assumed they were putting on airs. That’s when I met William.
He grew up running his family’s clothing store which had been open since before his grandparents were married.
Felt like punching him in the face. Finally, after battling myself not to stare too hard, I turned to him and asked, “Don’t you guys basically DIE in those things?” I was drenched in sweat wearing khakis I thought were reasonably breathable. This man had a sleeve rolled up exposing more cotton than my entire outfit.
And he was wearing madras. He chuckled, gestured at his getup that looked ready for the polo fields of summer camp and said, “My grandfather wore three-piece suits every day until he retired. And even after air conditioning, he’d wear a jacket and tie in August, even here in Charleston.” And the sweat just rolled off him. “I guess this,” he said pointing to hisCurrently shirt, “this is us being casual.” To say that struck me would be an understatement.
Once I started paying attention, I saw this same phenomenon pop up everywhere I travelled. Weekend visits to see family. Mini holidays.
Business trips. I started to ask questions. Talk to guys dressing differently than those back home.
Notice patterns that told stories far deeper than what we see on Instagram or what Menswear bloggers are wearing this season because some designer told them to. Southern men love their American style staples. They take devotion to tradition and classic looks to a whole other level.
I’ve encountered bow ties casually worn on Tuesday mornings for no apparent reason. Guys cracking out seersucker in 90 degree weather. Tweed jackets shrugged over polos during a three week winter “cold snap.” They’ll happily argue that dressing well is a sign of respect.
Respect for yourself. Respect for where you’re going. Respect for the occasion, even if that’s just grocery shopping.
I met a lawyer in Mobile once. It was ninety degrees and humid as balls, and he was wearing a pastel-coloured bow tie and pencil shirt. When I asked him why, he looked at me like I was crazy. “It’s a sign of respect.” He said.
This mentality runs deep in the South, and it crosses generations. You’ll notice young guys veering away from some traditions like wearing navy for every occasion, but they know the game. Their casualwear tends to be less “loud” as you move through other parts of the country.
Where else will you find guys that embrace getting shirtless in summer over looking “too trendy?” While men in other parts of the country sprint toward “casual,” Southern dudes keep it crisp on weekends. Tailored shorts vs. cargo. Polos or button downs vs graphic tees.
Loafers vs sandals. Guys down there have cracked the code of being comfortable while looking effortlessly together. Things shift once you cross over the Mason-Dixon Line and into New England.
Similar sartorial traditions exist there (prep! ), but it comes off slightly more structured and tailored. Those Bean boots were born out of function, not fashion. Moose crossed the road in New England?
Now you know WHY they’re wearing those Bean boots. The region’s affinity for waxed cotton, heavy knits, layering, tonal colour schemes… suddenly makes sense when you consider how quickly weather can kill you up there. Robert owns a shop on the coast of Massachusetts.
His grandfather started it, his father grew it up, and now he’s branching off on his own. When he told me, “If something’s expensive here, it damn well better earn its price tag through quality and longevity. It doesn’t shout ‘look at me!
I’m expensive’.” That, my friend, is true New England for you. Of course this shifts with income level. Head to fancier towns and neighbourhoods (Boca Raton, Beacon Hill, Greenwich) and you’ll notice things leaning luxe.
Cashmere jumpers that’ll run you $500+ but don’t scream their price tag. Tapered flannel trousers. Shoes you could bathe in gold paint and still outlast.
Strip away the luxury brands and you’ll see a similar appreciation for pieces that stand the test of time throughout working-class New England. Start pointing at Carhartt jackets, Red Wing boots, heavyweight flannels that could probably survive the apocalypse. Because that’s what they’re made for.
Practicality. Surviving harsh winters where dressing nicely isn’t an option, it’s a necessity. Minneapolis will introduce you to Midwestern guys who effortlessly blend coastal influence with lifestyle here in the heart of the country.
In July I met a software developer that owned four DIFFERENT parkas. Each were engineered for a different temperature range and he was NOT kidding about the weather. “You can’t be funny with winters here,” he said. “Some guys here just dress to not freeze to death. You’ve gotta layer, and you’ve gotta have clothes that can actually protect you when it dips below zero and you’re dealing with negative windchill.
It’s a whole thing.” Duh. Head farther inland and you’ll discover Rural Midwest has its own thing going on. Carhartt may be a fashion statement elsewhere, but out there it’s everyday uniform.
There’s still a sense of “good” clothes that I found really interesting out there. Good jeans (dark wash, no holes), good flannel, good boots. It’s a way to dress up that maintains some of the region’s distance from coastal professionalism.
I saw it best at my cousin’s wedding in Wisconsin. Dozens of men rocked their “best” jeans with a button-down shirt and some even threw on sport coats. In Chicagolllama,,,, NOPE.
But out there? Made perfect sense. When most people think of West Coast style, they think BUTTONS .
Too many_UNIQUE to name. Spend some time with West Coast men and similar patterns start to emerge. Pacific Northwest guys will teach you that Patagonia jackets, hiking trousers, and trail runners can handle work, school, and everything in between. “We don’t dress for the job we have,” said one Portland creative director. “We dress for what we’re doing after work.” His entire office wardrobe could have doubled for hiking or cycling outfits.
See those weathered Gore-Tex jackets I keep mentioning? They’re everywhere here. As are hiking trousers as trousers and “snow shoes” you could probably double as boots for.
My California learnings are best summed up by splitting the state in two. San Francisco-style menswear is largely refined workwear. Think selvedge denim,constructed knits, versatile outerwear that can withstand the city’s weird micro-climates.
LA style is its own beast. More liable to mix vintage workwear with designer tips to turn heads. Hollywood flash and beach cool colliding into an entirely new aesthetic.
That’s because “In LA, men have this freedom to experiment,” said stylist David Mansui. He splits his time between NYC and California. “Men on the West Coast are less afraid of colour, prints, patterns, variations in silhouette. The weather allows for it, and Hollywood allows men to get away with bolder personal style.” Native American influences and Western ranching tradition have had a major impact on men’s style throughout the Southwest.
From Santa Fe to Tucson to Albuquerque you’ll start to notice men wearing silver concho belts, bolos, Western shirts with pearl snaps and it… works. It doesn’t come off as costume. It’s authentic to the region’s cultural context.
Albuquerque shop owner Miguel Tineo put it best when he told me, “To someone from Chicago wearing these things is playing dress up. But to us, this isn’t fashion. This is our heritage worn as clothing.” And that, my friends, is the beautiful part about regional style differences.
It’s about so much more than climate. Old industries leave their mark. New England will forever have maritime ties littered throughout their regional style even while most men work offices instead of boats.
Western style will influence all of Colorado, Arizona, and New Mexico regardless of whether you’ve ever worked a ranch in your life. Even locally-admired public figures shape regional style long past their expiration date. Seattle may have created grunge but the layered looks they made popular are worn strongest today throughout the PNW.
Southern Cali’s surf and skate culture bleed effortlessly into every guys weekend wardrobe no matter where you are in SoCal. And NYC will influence males thousands of miles away that will never set foot in the city. So why do these regional styles persist in an age where we’re constantly being SOLD the same clothes?
Where retail chains make it easy to dress identically to the guy next door? Where online shopping lets us buy the same thing someone wears in Hawaii while we’re sitting at our desk in Denver? hell forbid you try and catch them wearing matching outfits. Case and point: workwear.
That heavy-ass Carhartt jacket dad’s been wearing since before you can remember? Urban dudes who’ve never seen a piece of farmland will hunt down vintage Carhartts and XCеляке oversized pieces to say they’re “authentically” wearing workwear. They’re wearing similar garments for the exact opposite reason.
Businesses like the one I visited in Charleston profit off these regional differences. They don’t compete with national brands by undercutting prices on basics. They hyper specialise in their regional style.
Custom lightweight suits engineered for Southern summers. Patterns and designs you can only find there. Hell, even your grip on “business casual” will vary by region.
Trust me. I’ve seen guys assume that what works in Houston will work when they travel for work. Only to discover they’re overdressed in Denver and underdressed in Atlanta.
Regional style matters because where you’re from heavily influences not only what you wear but how you dress. A Boston bro wearing a heavy wool jumper in Texas won’t just look out of place… they’ll look like they don’t understand how to dress for that climate. Same goes for a Cali casual guy wearing outdoorsy trainers and baseball hat to a meeting in Chicago.
Damn right that Northern dude’s wool jumper keeps him warm in Boston. But it rains there. Not hail like Texas.
Hell no. If you live somewhere with four seasons, realise that “winter clothes” will come off totally different depending on where you are. Don’t get caught wearing New England stylish boots downtown LA.
Unless you’re ready for questions. Regionality can make or break your travels. Some of the most embarrassing clothing moments of my life happened while travelling and forgetting where I was vs where I was from.
I know guys who refused to listen and continue to look like idiots when they leave their hometowns.
Understanding your environment, your history, and the community around you goes a long way in dressing well. And in a world selling us ghost clothing discarded at the first sign of discomfort, regional styles teach us about connection to place.
Back to William. When he wore that jacket on a hot ass summer day in Charleston he wasn’t ignorant of his climate. He was paying homage to generations past busting their asses to put theirs where his family is today.
Dressing well enough to earn respect when they walked into a room. Next time you travel, start noticing regional styles of men where you go. You’ll be surprised how subtle some of it is and how complex once you start digging into the deeper “whys.” Learn from it.
Have fun with it. But most of all, appreciate that we’re not all Nike sweatshirts and Adidas shorts in America. Trust me, you’ll thank yourself later.
