I walked into that startup office last month wearing what I thought was a perfectly reasonable gray suit – lightweight, unlined, basically the most casual tailored clothing I own – and got asked if I was coming from a funeral. The CEO actually said that. Out loud. While I’m standing there trying to figure out if this is some kind of test or if he genuinely thinks showing up in anything nicer than athleisure means someone died.
This is my life now. I’m the weirdo who still wears suits when literally nobody else does, and honestly? I’m fine with it. Well, mostly fine with it. There’s still that moment of panic when you realize you’re the only person in the room wearing actual pants instead of whatever hybrid jogger-jean thing everyone else has adopted, but I’ve learned to roll with it.
The thing is, I never set out to be the suit guy. Growing up in Sacramento, my dad wore khakis and polo shirts to his IT job every single day – same uniform, zero variation, peak engineer practicality. My approach to clothes for most of my twenties was basically the same: jeans, t-shirt, hoodie, repeat. Classic tech guy wardrobe. I had probably fifteen identical hoodies in different colors and thought I was being efficient.
Then I moved to my tiny SF apartment four years ago and had to actually think about what I owned. Going through my closet was this weird wake-up call – I had all this stuff I never wore, including a suit I’d bought for my cousin’s wedding that had been hanging there for two years untouched. But when I tried it on again, something clicked. I looked… good? Like, actually put-together instead of like someone who’d grabbed whatever was closest to the bed.
Started wearing that suit more often, just because I could. Wore it to dinner, wore it to work occasionally, wore it to parties where everyone else showed up in jeans. And yeah, people noticed. Some thought it was weird, but others kept asking where I got my jacket or telling me I looked sharp. The reactions were interesting enough that I kept doing it.
Building a minimal wardrobe forced me to think harder about what I actually wanted to own, and it turns out I wanted to own clothes that made me feel confident. Suits do that for me in a way that hoodies never did. There’s something about the structure and the fit that just works – I stand straighter, I feel more pulled together, conversations happen differently. Maybe it’s all in my head, but if it is, it’s working.
The trick I’ve figured out is that you can’t wear a suit like you’re apologizing for it. Nothing screams “uncomfortable” louder than a guy constantly adjusting his jacket or fidgeting with his collar. My friend Marcus wears suits to his tech job and always says it’s like wearing a band t-shirt – this is just what he’s into. Some people collect sneakers, he collects suits. That confidence is everything.
I’ve also learned the art of the preemptive joke. When I walk into a room and realize I’m overdressed by about three levels of formality, I’ll make some comment like “Yeah I know, I’m the only guy with a tie – apparently I missed the memo about casual Friday expanding to the entire week.” Gets the awkwardness out of the way and lets everyone move on. Most people actually appreciate that you’re not taking yourself too seriously.
The modern suit game is different anyway. I’m not talking about stiff Wall Street power suits with enormous shoulder pads. My favorite pieces are unstructured cotton blazers that feel like wearing a really nice sweatshirt, lightweight wool that moves when you move, stuff that looks tailored but doesn’t feel constraining. Half the time I’m wearing suit separates with casual pieces – navy jacket with chinos instead of matching pants, oxford shirt instead of a dress shirt, sometimes even clean sneakers if the setting allows it.
COVID actually helped with this weirdly. When everyone’s dress codes completely collapsed and half your meetings became Zoom calls where nobody could see your pants anyway, the concept of being “overdressed” started feeling meaningless. If your coworkers are in hoodies and you want to wear a blazer, who cares? We’re all just making it up as we go along at this point.
The office holiday party last year was when I realized I’d fully committed to this approach. After years of “festive casual” parties where everyone wore the same nice jeans and button-down combo, I decided to wear an actual tuxedo. Not because the dress code called for it, but because when else was I going to wear the thing? I’d bought it for a wedding and it was just sitting in my closet.
Definitely had that moment of panic walking in – I looked like I was attending the Met Gala while everyone else looked ready for a barbecue. But then something interesting happened. All night, people kept coming up to talk to me. The CEO, who I’d barely spoken to before, spent twenty minutes chatting about whiskey. Women kept telling me I looked great. Men asked about my tailor. The tux wasn’t just clothing, it was like this social catalyst that gave people a reason to start conversations.
That’s when I stopped thinking about suits as following some outdated dress code and started seeing them as social strategy. Dressing up isn’t about imposing formality on other people – it’s about using clothing to create the kinds of interactions you want to have. Sometimes being the best-dressed person in the room opens doors. Sometimes it starts conversations. Sometimes it just makes you feel more confident, which affects everything else.
Of course there are limits. I learned this at a tech conference in Austin where my linen blazer and chinos still managed to mark me as “the suit guy” among a sea of startup t-shirts. In those environments you have to make some concessions – knit tie instead of silk, denim shirt under the jacket, small signals that you get the vibe but you’re interpreting it your own way.
Seasonality matters too. Nothing looks more out of place than being the only person in wool when it’s ninety degrees outside. My summer rotation is heavy on cotton and linen – materials that look intentionally casual instead of formally stiff. My favorite warm-weather jacket is this faded blue cotton thing I’ve washed so many times it feels like a sweatshirt but still has the structure of proper tailoring. Pairs perfectly with a white t-shirt and jeans when I want to look put-together without looking corporate.
Color helps too. Those conservative charcoal and navy suits that were office staples can look pretty funereal in today’s casual workplaces. I gravitate toward lighter blues, soft grays, earth tones – colors that signal I’m wearing this because I want to, not because some dress code is forcing me to. My olive cotton suit gets more compliments than anything else I own specifically because it doesn’t look like standard business attire.
The accessories game has changed completely. Power ties and perfectly folded pocket squares look try-hard now. I stick with knit ties, linen pocket squares stuffed casually instead of folded precisely, minimal jewelry beyond a watch. The goal is looking thoughtfully put-together without seeming studied or stiff.
Even how you buy suits matters now. Those heavily structured 80s power suits look like costumes today. I work with a tailor who specializes in what he calls “taking the business out of the suit” – maintaining the clean lines that make tailoring flattering while removing the corporate stiffness. Natural shoulders, relaxed cuts, less padding in the chest. Still looks sharp but doesn’t scream “BUSINESS” in all caps.
The hardest part isn’t actually the initial entrance when you realize you’re overdressed – it’s maintaining confidence throughout the day as you continue to stand out. I’ve developed mental tricks for this. Most people are too worried about their own appearance to spend much time judging yours. Focus on how the suit makes you feel rather than how you think others perceive you. Remember all the times you’ve gotten compliments from people who initially seemed confused by your formality.
There’s definitely psychology at work when you’re the best-dressed person in the room. You’re signaling confidence, attention to detail, willingness to stand apart – qualities that tend to command respect in professional settings. Multiple bosses have told me they initially thought I was overdressing to compensate for something, only to realize later it was just my personal standard. One admitted he started paying closer attention to my work because “anyone who cares that much about appearance must be detail-oriented elsewhere too.”
My approach now is pretty simple: I wear what I want, but I pay attention to how it affects my interactions. If a suit creates distance when I need connection, I adjust. If it opens doors and starts conversations, I lean into it. Sometimes I’m the only person in a tie and that’s fine. Other times I leave the suit at home because the situation genuinely calls for something more casual. The key is making these choices deliberately instead of defaulting to either extreme.
The best compliment I ever got was from my friend David who works at one of those stereotypically casual startups. After seeing me in various suits at social events for years, he told me “I never think of you as the guy who wears suits. You’re just Ruth who happens to dress better than the rest of us.” That’s the sweet spot – when your clothing becomes so integrated with who you are that people see past the fabric to the actual person.
So if you’re considering joining the small but stubborn group of people who still wear tailored clothing in a hoodie world, go for it. Find the level of formality that makes you feel confident rather than conspicuous. Invest in pieces that fit your actual life, not some fantasy where you’re attending board meetings every day. And remember that real style has always involved standing out – just make sure you’re doing it on your own terms, not because you’re trying to prove something to people who probably aren’t paying that much attention anyway.
Ruth lives in San Francisco and swears by “fewer, better things.” His posts explore minimalist wardrobes, quality basics, and dressing intentionally without turning fashion into clutter. Practical, efficient, and quietly stylish—just like his closet.
