Last month I wore a grey suit into a startup office for the first time and was asked if I was “sporting attire from a funeral”. I kid you not. The CEO of this company looked me dead in the eye while I was standing there debating whether this was some sort of joke and said, “Would you wear this to a funeral?” I work in tech.
In San Francisco. My “suit” was lightweight grey slacks and a semi-unstructured gray blazer. The most casual business clothing I own.
Ever since then I’ve thought of myself as that guy. The dude in jeans and t-shirt wearing who secretly judges everyone else’s closets.
And hey, don’t get me wrong, I kind of love it.
Most of the time. Sure there’s a second every time you walk into a room and realize you’re the only person not wearing distressed jeans and a t-shirt, but you quickly get used to that. What I’ve never understood is why I ended up here.
I never intended to become “the suit guy”. My dad wore khakis and polo shirts to his IT job every day growing up in Sacramento. Didn’t vary an article of clothing one way or another, Ballmer jeans engineer level default.
Same thing for me through most of my twenties: jeans, t-shirt, hoodie. Rinse. Repeat.
Basic tech bro warddrobe. Probably owned fifteen identical black hoodies in varying shades. Thought I was being efficient!
I moved into my SF apartment four years ago and realized I actually had to think about what I owned when I unpacked. Sorting through my closet was a semi-clinical experience. I owned way more clothes that I wore than I realized.
Including a dusty suit that I’d purchased for my cousin’s wedding two years ago that had never seen the light of day since. But for whatever reason, it fit. And it looked… good.
Not hood-ie-shirt teezy kind of good. I actually looked like I tried. So I started wearing that suit around because I could.
Dinner? Sure. Work?
Sometimes. Parties where everyone else showed up in jeans and t-shirts? Yup.
And you know what happened? People said stuff. Some people asked questions about how it wasn’t “regular clothes” and looked at me weird.
But other people asked me where I got my jacket or complimented me on looking “dapper”. Weird comments became enough of a novelty that I kept wearing it. Curating a more minimal wardrobe made me think more about what I actually wanted in my closet.
And do you know what I found I wanted? Clothes that made me feel good. I love how a well-tailored suit makes me feel.
It’s a confidence thing. I’ve never been someone who rocked the hoodie life. Somehow putting on a nice shirt and blazer makes my neck stand up straighter.
I feel more “gether” together. People treat me differently. Maybe it’s all placebo, but if that’s the case, I’m glad there’s some science backing my outfits.
The one thing I’ve learned? You have to wear a suit like you got it. There’s nothing worse than some dude sauntering around adjusting his jacket every five seconds because he clearly doesn’t know how to wear a tie.
My friend Marcus wears suits to work at his tech job. He says it’s like rocking an old band t-shirt. “This is what I like wearing, deal with it.” Those that know him are used to it. They don’t care because he exudes confidence.
Be that dude. My other trick? Throw them off with humor.
Learn to make a joke at your own expense about how you know you’re overdressed. “Yeah I know, I’m that guy with the tie… must be casual Friday across the whole company now.” Something about letting people know you know you don’t fit in lets them know it’s okay to talk to you. Most people love that you don’t take yourself too seriously. Suits these days are nothing like they used to be.
We’re not talking about stuff pumped full of shoulder pads that make you feel like a fatty. I’m talking lightweight wool that flows as you move, unstructured cotton blazers that feel like luxury sweatshirts. You can totally get away with wearing suit separates with jeans.
Pair that navy blazer with chinos instead of a matching suit pants. Or wear an oxford shirt vs a button up. I keep a pair of clean white sneakers at the office for days I want to dress up without looking… stuffy.
COVID actually made this easier in a lot of ways too. Ever since everyone’s dress codes were thrown out and half your coworkers you only see on Zoom (aka pants aren’t required), the concept of “overdressing” just seems weird. If your team is wearing hoodies and you want to throw on a blazer?
Who cares? But nothing made me realize I’d fully embraced my new attitude than our office holiday party last year. You know how these things usually go where “festive casual” equals nice jeans and button-up for everyone?
I wore a freaking tuxedo. Something about being locked in the house for a year made me decide “screw it, might as well wear the tux”. I never wore it after buying it for a wedding and it had been hanging in my closet collecting dust ever since.
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Of course I had that panic moment where I walked in and felt like everyone was staring at my skinny tie. Felt like I won a paranormal investigation show’s costume contest while everyone else wore sweats. But then something cool happened.
People started coming up to talk to me all night. The CEO of the company who I’d normally only say hi to in the hall kept me chatting for twenty minutes about whiskey. Women told me I looked “nice”.
Men asked me where I got my jacket. It was the hugest confidence booster because that stupid tux became a conversation starter with people I wanted to impress. That’s when I changed my mindset.
Rather than feeling like I had to dress to some outdated standard, I started viewing dressing up as a tool. If you want people to take you seriously, dress seriously. If you want to start conversations, wear something that will differentiate you from the herd.
Clothing can be your social lubricant if you use it correctly. Now sure, there are definitely still times when I have to tone it down slightly. Color me surprised when I wore a linen blazer and slim pants to a tech conference in Austin and was immediately hailed as “the suit guy” to a room full of startup employees rocking t-shirts.
Guess I couldn’t blend in completely. But that’s okay. You just learn to make small concessions.
Wear a knit tie instead of silk. Throw on a denim shirt under your blazer. Give people subtle hints that you get the culture but you’re going to take it however you want.
Weather matters too. Seriously nobody wants to wear wool in the middle of summer. My go-to summer uniform is light cotton and linen suits.
They feel effortlessly casual as opposed to stiff and formal. My favorite summer jacket is this worn in blue cotton number I’ve washed so much the color comes out that still retains just enough of a blazer shape to not look like a sweatshirt. Throw it over a white tee and jeans and it’s my go-to casual but still got-it-together outfit.
Color is another thing I’ve embraced. Don’t get me wrong, light grey and navy are classics for a reason. But wearing those sad sacks of charcoal modern day makes you look like you’re going to a funeral… which might as well be what we’re all doing these days.
Instead I opt for lighter blues and grays, earth tones, anything that doesn’t read stiff or corporate. My olive cotton suit is my new favorite thing because nobody expects a suit in that color to not be some boring business attire. Not to mention how your whole accessories game has to change.
Big box store ties and aggressively ironed pocket squares are so 2010. I keep my accessories minimal these days. Knit ties.
Linen pocket squares stuff thrown in my jacket casually instead of folded like a masterpiece. And that’s about it. Minimal jewelry.
I wore a watch today and called it a day. Even how you buy suits is different now. Big and stiff 80s power suits are vintage now.
I have a tailor who basically takes “business” out of your suit. All the clean lines that tailoring can provide that help cut bullshit from your jacket, but without the huge shoulders and chest padding that made folks run from anything fancier than a button up. Natural shoulders, relaxed fit, and less padding.
Business casualdentity crisis. And here’s the real challenge. It’s not walking into a room and knowing you’re over dressed.
It’s having the confidence to walk around all day knowing you’ll stick out. I like to remind myself that most people are too self absorbed in their appearance to care what I’m wearing. Make yourself the exception and focus on how amazing you feel wearing that stupid blazer.
Remember every time someone said something to you about your outfit who previously gave you sideways glances. The truth is wearing a suit does play mind games with people. You’re presenting yourself as a man of power and confidence.
Details matter when you wear a jacket and people notice. I’ve had multiple managers assume I was wearing a suit to make up for deficiencies in my work before they got to know me. Only to come to find out later it was just my standard work attire and I didn’t give a crap what they thought.
One of them even told me he paid more attention to my work because “someone that cares about how their clothes look has to pay attention to details at work too.” These days I wear whatever I want, but pay attention to my surroundings. If a suit makes me feel overdressed and cuts people off I’ll adjust. But if it lets me own a room?
Fuck it, I’m wearing a tux. The best thing anyone’s ever said to me about my style? My longtime friend David who works at an embarrassingly casual tech company said “I never think of you as the suit guy, Ruth.
You just look like Ruth… who dresses nice.” And there it is. My goal these days. Wear suits until they become you.
Not because you came to the office, but because THAT’S WHO YOU ARE.
If you’re reading this and thinking about breaking out the jackets yourself. Do it.
Wear suits because you want to. Just remember not to go too crazy. You don’t want to look like you’re wearing your dads’ suit.
Learn what works for your lifestyle and go from there. Stick to solids. Find a tailor you trust.
Two words: Suit jacket. Invest. Real style has always been about standing out.
Just make sure you’re doing it on purpose.
