The Subtle Flex of Being the Fashionable Guy in the Office
Illustration: Michael Kennedy

The Subtle Flex of Being the Fashionable Guy in the Office

Am I the only one having withdrawals from wearing my fall fashion work wardrobe?

I don’t know about you, but head-to-toe loungewear has officially lost its appeal. The home office perks of all-day PJs, pantless video calls (no Toobin), and sporting the same sweatshirt three days straight don’t hit like they used to now that cooler temperatures have become the norm. Autumn, my friends, is where I thrive. I don’t love fall only because of the balmy weather and omnipresence of pumpkin spice (don’t knock it ’til you try it) — it’s also the season when I get my best ’fits off. And I’m bummed that I’m missing out on it this year.

Even the idea of planning a work outfit is something I high-key long for. Waking up in the morning, having my breakfast, and thinking, Hmm, what will I wear to stunt on my colleagues as I make a fashionably late arrival to work? Because if we take the whole paycheck thing out of the picture for a second, getting first-day-of-school fresh for work is half the fun of the job — especially if you work in a city. Fall is peak office-style season; when sweat stain worries and full-blast air conditioning are a thing of the past, it’s safe to break out the layers, textures, and colors waiting patiently in the back of the closet.

This year, I was emotionally ready to throw on my best cashmere, my cardigans, and to channel Lenny Kravitz via oversize wool scarves. I had plans to bring the drama in my long wool coats, flex in my collection of turtleneck sweaters, and add a drop of sophistication with my Chelsea boots. They’ve been collecting dust for so long that sometimes I just want to wear them while I’m taking out the trash. Sure, I’m aware of how silly I’ll look on the curb with my Air Brunch 1s, sweatpants, and a robe, but they come on, they need some face time. And I’m not even a huge sneakerhead, but I’m good for slipping on a crisp pair of Nikes or Adidas to top off my tech dad starter pack ’fit — clean kicks, patterned wool socks, rolled-up chinos, a beanie, a Casio watch, and a pair of Warby Parkers.

Fall is peak office-style season; when sweat stain worries and full-blast air conditioning are a thing of the past, it’s safe to break out the layers, textures, and colors waiting patiently in the back of the closet.

When I would commute, I’d love to people-watch and check out what folks were wearing. Granted, the trend out here in Seattle is basic, but every now and then there are some that surprise me. I’d spot a pair of sneakers that I never considered pairing with a pair of chinos, or mentally bookmark a North Face puffer jacket I might just cop for myself.

Dressing up for work is obviously something I love doing for myself, but it was nice knowing that it was appreciated, even expected, when I walked into the office. The added bonus to feeling like a million bucks when you walk out the door is having unofficial fans to witness it. It’s one thing to be one of the very few Black people in the office, but also be one of the best-dressed on top of being good at your job? It’s a triple threat.

A quick “Love your shoes!” down the hall or a scan and head nod combo in passing does something for the spirit. I had a really cool Asian co-worker who’d also dress to the nines, so we’d always compliment each other tit-for-tat.

“Okay, I see your shoes. I might have to steal that.”

“Nah, I see you with the trench!”

You gotta have that one co-worker where you can quickly bounce the flex off each other in front of people before getting back to work. My friends and I will even drop a quick mirror flick in the group chat on our good days, to take notes and gas each other up there. There’s a friendly competitiveness to it, and banter that helps the workday feel a little lighter. That sort of thing just isn’t the same over Teams and Zoom meetings.

When I thought about all the things I wouldn’t miss about going back to the office, I didn’t realize how much I’d crave for those little moments to shine; those moments where I get to show up as myself and be expressive about who I am without people prying into my personal life. What I’m wearing says plenty.

And looking down at my tired gray sweats and the hole in my sock, what I’m wearing now says that I need to shed the worn athleisure gear, find an errand to run, throw on some intentional threads, and remind myself that I still got it — office or not.

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