Eight years ago, I was griping to my wife Margaret about how sterile my thoughts on clothing had become. I’d write stuff like this blog post about the merits of waistties versus belts or pontificate about lapel shapes or whatever, but almost none of it ever applied to how most American men dress on a daily basis. “Have you tried talking to anyone who doesn’t work in an office?” she asked me that night, in that tone of voice that means “Hint hint, bitch please.”
She’s smart.
Ever since then, I’ve done my best to talk to anyone who’d let me shadow them around their workplace. Schoolteachers. Nurses. Police officers. Firefighters. Factory workers. Construction crews. The aim was always the same – talk to guys who, for one reason or another, can’t just throw a blazer over their outfit and be done with it. Who’ve had to learn how to think about style from the ground up.
These are the guys who taught me more about style than Reddit or Styleforum ever did.
David taught me how uniforms don’t have to be boring.
I visited his third-grade classroom in the suburbs of Philadelphia last spring as he was getting ready to start his school year. One thing I quickly realized chatting with him was that he and I finally solved the same problem twenty years apart – he knows that the best clothes are ones you don’t think about wearing.
Teachers chasing around eight-year-olds all day know that their clothing is their armor. They get gum smushed into their shirts, they get food stains, they get clumsy hands grabbing at their pants. They need clothing they can throw in the washer on hot and never think about again.
David solves all these problems with the simplest trick – performance polo shirts in solid colors. Bright solid colors that actually somewhat resemble business shirts, but that can be washed hundreds of times without losing their shape or color. He only needs two or three at a time because he can wash them with hot water and never worry about it.
He wears only stretchy chinos in darker colors – “Navy and black fade the least, plus I can grab my knees on these if I need to without worry” – and always has a backup pair at school in case of accidents. His favorite pair has a weird stain on the ass from a kid’s art project last year that he just can’t get out, but that’s his favorite pair because they fit the best.
He told me “Teachers get a lot of joy out of humiliating students for goofing off or not working hard enough, but we should take the same approach to our clothing. Challenge students to find the oatmeal stain, or whatever. If they can’t, you did your job.”
To top it all off, he wears athletic sneakers with leather tops that resemble dress shoes from across the room. He swapped out his dress shoes for these after the first week of his first year teaching when he developed plantar fasciitis from standing around all day in unsupportive footwear.
The brilliance of David’s entire approach hit me when we were talking about watches. Like me, he only wears watches he doesn’t care if they get damaged – only sport watches and utilitarian digital watches with no jewels or moving parts that are just there to tell him the time. Every item of clothing he wears to work is dedicated to the task of not distracting him from his job, and serving him well while he does it.
Teachers have barely any downtime, and David dresses like it. His entire focus when it comes to clothing is function over anything else. And yet his shirts always look intentional, his pants always look clean. He has developed an entire aesthetic centered around not caring about his appearance.
“How do the kids react?” I asked him.
“They know when I take pride in my appearance, and they appreciate it. The kids don’t care if my shirts are $30 or $300, but they notice when I look lazy or like I didn’t put effort into coming to school.”
The eternal battle of caring about what you wear versus not caring what you wear. David has found the sweet spot.>>
Marcus taught me you can have style within constraints.
Thanks to Margaret’s sister Kate, I was able to meet up with Marcus, a cardiac nurse who works the night shift at Jefferson. Scrubs are a weird thing to figure out from a style perspective because there’s only so much room to actually “dress up.” But when I showed up to meet Marcus at a coffee shop near the hospital, he looked ten times more professional than any doctor I’ve ever met.
“It’s all in the fit,” Marcus said. “Most nurses just buy scrubs in whatever size they think they are and call it good. But if your scrub top is sagging off your shoulders or your pants bunch up at the ankles, you look sloppy. Invest in well-fitting scrubs and you’ll look ten times more professional.”
He explained that he spent way too much money than he should have on a brand of scrubs that are tailored to actual body shapes instead of designed to cover bodies. The results were basically night and day compared to most medical professionals I’ve encountered. Still clearly hospital scrubs, obviously professional, but just dressed with more intention.
Little things stuck out to me when I was talking to Marcus. He always wore undershirts with his scrubs that were fitted and always matched or complemented his scrub color. His socks were compression socks but they had subtle patterns and weren’t anatomically white. His shoes were all high-end, high-performance athletic shoes that looked sterile and clean but could handle twelve-hour shifts landing on him hard.
“I spend more on shoes than the average dude spends on their whole work wardrobe,” he said. “But my feet are my livelihood. If they hurt, I can’t help patients. Shoes are where I spend most of my money.”
Doctors and nurses get harassed about their clothes all the time but few have thought about style in their off-hours like Marcus. Talking to him made me realize how guys who have to work within clothing constraints during the day tend to focus on clothes more when they can wear what they want. Marcus dresses to the nines on his days off.
More importantly, Marcus dresses like he wants to whenever he can. He told me “By the time I leave work I just want to throw on pants and a tee and call it good. But on my off days I force myself to wear jeans, button ups, real leather shoes. It’s like my brain needs to be reminded that I have other clothes.”
Ironically, men with the most restrictions during the day often enjoy dressing up more than I do in my free time. I had no idea.
Tony taught me that different doesn’t have to mean worse dressed.
Tony’s story was probably the most unique of any of them. A general contractor who builds luxury homes around the Main Line, Tony’s work clothes consist primarily of Carhartt pants, work boots, and whatever long sleeve won’t get ruined on an job site. When I met him at his workplace, his office was his truck and his shirt was covered in sawdust.
“Work clothes and ‘real clothes’ are two completely different things to me,” Tony told me when we sat down in his truck to chat. “Work is work, when I’m there I’m just trying to survive and get done. My weekends and nights are when I get to wear nice clothes and feel awesome about how I look.”
He dressed well for our interview, but I wanted to see what he wore to work so we spent thirty minutes driving around his current project while he showed me his arsenal. High-end men’s clothing store quality casual clothes hung in his closet at home that he wore on the weekend, but his work clothes were where it got really interesting.
Tony took pride in every single thing he wore to work. His jeans were from high-quality work jeans brands that cost him 3 times what most dudes spend on their work jeans but last him twice as long and look like they were actually made to fit his body. His work shirts were all from the same brand and all the same style but in different colors that he ordered online in bulk after finding something that worked.
Most impressive of all? Tony’s boots.
These dudes spend their lives on their feet, and Tony told me he throws down a lot of money on a good pair of boots that will last. American-made boots with thick rubber soles that he had repaired multiple times since he bought them rather than simply replacing them.
“I’m nearing eight years with these Red Wings,” Tony said proudly. “They’ve been resoled twice, but each time they feel brand new. Most guys don’t care about their boots and just buy another pair when the sole gets worn down. I could do that too but these boots just fit my feet like I was custom-made.”
All of these guys approached their wardrobe the way I approach mine, they just did it with different clothes. David wears chinos that fit his body and allow him to do his job comfortably instead of jeans. Marcus has streamlined his shoe game down to purely things that provide support and look sterile enough to work in a hospital. Tony views his boots as long-term investments that he maintains instead of constantly buying new pairs.
There’s a formula to dressing well that every single guy I met recognized, even if the clothes they used it with were completely different than mine.
Maybe you think that because you wear Carhartts to work you couldn’t possibly take advice from a guy who wears suits every day. Think again.
Proper fit is important whether you’re wearing expensive suit pants or expensive work pants. Investing in quality matters whether you’re buying dress shoes or boots. Having a system for buying and maintaining your wardrobe will help you no matter what you wear to work. And if you don’t care what you look like at your job, why should anyone else?
I still work in an office and will for the foreseeable future. I haven’t adopted performance polos into my wardrobe just yet. But talking to these guys and learning the thought processes behind how they dress has influenced how I think about clothes and style in ways I never would have expected. Maybe it will for you too.
