The Real Working Men Who Haven’t Given Up on Looking Good

Last Tuesday I found myself in a staff room in South London that smelled like instant coffee and desperation, watching this English teacher named Tom get ready for what he called “the Year 10 circus.” The guy was wearing these navy Dickies chinos – you know, the work pants brand that somehow became cool again – and I’m thinking, here’s someone who gets it. His M&S shirt wasn’t anything fancy, but it fit properly and had that slightly better feel you get when you spend an extra tenner on thread count. The desert boots were properly beaten up, which frankly made them look better than they probably did new.

“Kids will throw actual things at you sometimes,” he said, rolling his sleeves with the kind of precision that comes from doing it fifty times a day. “But I’ll be damned if I’m going to dress like I’ve given up on life just because the job’s demanding.” That’s when I knew I’d found what I was looking for – real working men who refuse to surrender style to function. Over the past month I’ve been hunting down these guys across different professions, and honestly? They’re doing some of the most thoughtful dressing I’ve seen anywhere.

See, I spend my days in suits talking to other people in suits about very serious legal matters. But these guys – teachers, doctors, tradesmen – they’ve got to solve problems I never think about. How do you look professional when you’re crawling under a desk to fix wiring? How do you project authority with teenagers while staying comfortable enough to not hate your life? How do you inspire confidence in patients without looking so formal they can’t relate to you? These aren’t Instagram fashion challenges, they’re real life.

Take Tom’s approach to the heating situation – apparently British schools exist in some kind of thermal chaos where you can freeze in the corridor and roast in the classroom next door. His solution? Layers, but smart ones. Navy cardigan that comes on and off easily, cotton shirts that breathe properly, chinos with just enough stretch that he’s not adjusting himself every time he leans over a desk. “I learned this the hard way,” he told me, pulling on that cardigan as we walked through what felt like a meat locker masquerading as a hallway. “First year teaching, I’d show up in whatever, spend the whole day uncomfortable and looking like I’d been through a washing machine. Now I think about it.”

The footwear thing really got my attention. Here I am spending serious money on Church’s and Crockett & Jones because I want shoes that last, and I meet this art teacher in Manchester – Daniel – wearing Clarks Desert Treks that have clearly lived through six years of teenage chaos and somehow look better for it. “Cheap shoes will destroy your feet and your back,” he said, and honestly, he sounded like my father talking about shoe trees. “It’s the one place I won’t compromise anymore.” Made me think about how we often get the investment priorities backwards.

What really struck me was how these teachers think about color as communication. This history teacher in Bristol – Dan – has built this whole wardrobe around what he calls “documentary colors.” Olive, rust, tobacco brown… looks like he stepped out of a 1940s film about the war, which apparently helps with his World War II lessons. Meanwhile the chemistry teachers all wear dark colors because, as one put it, “chemical stains are inevitable and blue hides them better than white.” There’s strategy here that goes way beyond just looking good.

Then I spent a morning at the Royal London Hospital with Dr. Asif, who’s somehow managing to look completely put-together despite working twelve-hour shifts in the NHS chaos. His secret? What he calls “the uniform approach” – five versions of essentially the same outfit, but each piece chosen with obsessive attention to detail. Thomas Pink shirts bought on sale because they’re the only ones that stay crisp through a full day, navy and grey trousers with just enough taper to look intentional, shoes that can be wiped clean quickly between patients.

“I need patients to trust me immediately,” he explained, adjusting a shirt that had just enough stretch to let him move quickly if someone collapsed. “But I also can’t intimidate them. It’s this balance between competent and approachable, and honestly, most of it comes down to fit and fabric choice.” The guy gets it – presentation in his world isn’t vanity, it’s part of doing the job well.

What fascinated me about the medical crowd was their relationship with accessories. Dr. Asif showed me his Seiko automatic – practical for taking pulses but also just a nice watch. “Older male patients always notice it,” he said. “Sometimes it’s the only thing that gets them talking initially.” Smart thinking. In my world we use watches and cufflinks as conversation starters with clients all the time, but I’d never thought about how a GP might use the same principle.

But here’s where I got really surprised – talking to tradesmen. I’ll be honest, I expected pure function over form. Instead I met Mike, an electrician who’s put more thought into his daily kit than some investment bankers I know. Dickies work trousers because “they last years and the pockets actually work,” fitted base layers from Patagonia instead of regular t-shirts because “they handle sweat better and honestly look better too.” Then this Patagonia gilet that he wears like it’s part of his skin.

“Look, there’s this stereotype of builders with their arse hanging out,” Mike said, and I could hear the irritation in his voice. “Most of us take pride in how we present. We’re in people’s homes, dealing with their stuff. First impressions matter in my business too.” Made me realize how narrow my thinking had been about professional dress requirements.

The whole workwear evolution thing really got me thinking. These brands – Carhartt, Dickies, all the heritage American stuff – started as pure function, became fashion statements for people who never did manual labor, then somehow came back to actual workers who now appreciate both the function AND the improved aesthetics. It’s like fashion completing some weird circle.

Pete, this carpenter whose family’s been in the trade for generations, showed me his dad’s old work jacket next to his current gear. Night and day difference. “Dad’s stuff was purely practical and looked it,” he said. “Now I can get protection that also looks good when I’m meeting clients or grabbing a drink after work without changing.” Progress, right there.

The footwear investments really caught my attention though. Rob, a plumber wearing pristine Timberland Pro boots, explained his “van shoes versus job shoes” system. Keep the good ones clean for client meetings, let the work ones take the beating. But even the work boots are quality – “injury means no income in my line,” he said. “The style part’s nice but secondary to not getting hurt.” Practical thinking that somehow results in looking better.

What connects all these guys is this move away from traditional “work clothes” toward more thoughtful pieces that handle professional demands while letting personality show through. Technical fabrics that used to be only for hiking have moved into offices and workshops. Work brands have stepped up their design game. And everybody’s figured out that looking good, feeling good, and working well aren’t separate things – they support each other.

The other thing that struck me… these guys have all developed personal uniform systems rather than chasing whatever’s trendy. They’ve figured out what works in their specific environment and refined it over time. Quality over quantity, solving actual problems with clothing choices. There’s something we could all learn from this approach, regardless of what we do for work.

When I asked Tom what he’d tell new teachers about dressing for the job, his answer worked for everyone I’d met: “Buy less but buy better. Figure out what makes your working day harder and solve those problems with what you wear. And remember – students notice everything. They might not comment when you look put-together, but they definitely notice when you don’t.”

Watching him navigate that crowded school corridor later – cardigan off because of the heat, sleeves precisely rolled, those beaten-up desert boots moving confidently through the teenage chaos – nothing screamed fashion, but everything looked intentional. In one of the most demanding environments you can imagine, he’d found that sweet spot between function and style.

And really, isn’t that what we’re all trying to figure out?