Out of Uniform

Still dressing for a job no one is watching — on office rules, algorithmic style, and figuring out who to be when the room has changed.

I still dress for work every morning. Khaki trousers. A light blue Oxford button-down. Argyle socks. Brown leather sneakers. I shower, comb my hair, brush my teeth. I dab on moisturizer and spritz a bit of cologne in the air and walk through the mist. I grab my briefcase and head up to my “office” on the rooftop of my building, where I’ll set up my computer, roll up my sleeves, and get to work. 

Every morning I put on the uniform of a job I have given myself. It signals to me that I am working, I am producing, I am still part of society.

I did the same thing during Covid. Then, though, it was more of a grasp at normalcy, a way to find stability in a world rife with upheaval. When we first got sent home from the office in March 2020, I kept my routine intact. Same alarm. Same clothes. I’d mask up and go for a walk around the block as though I were headed to the train. I needed the ceremony. The preparation, the clothes, the shift in mindset that said: “this is work time.” And at the end of the day I could change my clothes, pour a glass of wine and declare the workday complete. Many folks I worked with at the time or friends I’d talk to opted out of “hard pants” in favor of sweats and that’s if they were wearing any pants at all. A full body mullet: business up top, party downstairs. Which, now that I write it, makes it sound way more fun than it was.

I’m not judging. I just needed the rhythm to keep me going. The ritual to keep me sane. 

I’m not a fashionista, but I am intrigued by fashion. I’ve seen both Devil Wears Prada movies. I’ll check who wore what after the Met Gala. I watched several seasons of the original Project Runway. I’d love to wear Dior or Yves Saint Laurent or Tom Ford. I do have one Gucci pocket square. 

Mostly, my closet is a tribute to business casual. A mini Polo by Ralph Lauren shop, only messier. I have a few things I like to call my braver pieces, but usually those don’t make it into heavy rotation and require a bit of gumption for me to actually wear. Vacation Ryan can pull off a lot more than workaday Ryan. I’ll look at an Instagram post from GQ and marvel at what Jacob Elordi or Pedro Pascal is wearing and wish I had the courage to pull it off. To be that confident. To look that good in yellow. 

As much as I’d like to branch out and wear more color or change up the silhouette, I am generally locked into the office look. It’s easy. I know the rules.

But calling it easy wildly underestimates the time it took me to learn the rules. I remember the gauntlet that was back-to-school shopping. My mother would circle the parking lot five or six times before we found a spot at the jam-packed mall. Every year we’d hit the normal spots: Kohl’s, TJ Maxx, JCPenney. I hated JCPenney the most. It felt especially cruel for an adolescent trying to survive the Darwinian microcosm of high school. JCPenney was at the mall proper, an anchor with its own massive entryway. My adolescent anxiety and melodramatic mind made me believe I’d die—DIE!—if anyone saw me go in there. At least the other stores were mall-adjacent and the only people that would see you there were the other people who were shopping there, a teenage version of mutually assured destruction. JCPenney was so close to the promised land that was Fox Valley Mall. If I ran for it, maybe I could break past the beige interior and get to Marshall Field’s, Abercrombie & Fitch, Structure. The real mall. I wanted to shop at the stores the popular kids shopped at. Back to school was an opportunity to reinvent myself, no matter what the family budget. I could emulate the California cool of Beverly Hills, 90210 or go a little grunge with a My So-Called Life-inspired look. I could wear discount Izod and Lacoste, I could go to The Gap and pull together a solid look. If I begged, maybe we could go to J. Crew. Anything that would help me ensure eighth grade, then ninth grade, then tenth grade would finally be the year of Ryan. Each September a chance to start anew.

Then the day would arrive. I would sift through my new clothes, try different combinations, assemble outfits only to toss them aside. My mother would shout at me to hurry up or I’d miss the bus. I’d grab what I thought would be a bold statement. A look that would signal I was part of the A crowd. I’d get on the bus only to realize I’d zigged when I should’ve zagged. That no matter what outfit I chose, it had the stench of try-hard, which, as anyone who has ever gone to high school could tell you, is immediately disqualifying for popularity. 

This “trying too hard” thing didn’t stop with high school. It carried on through college and into adulthood. I would put together a look, arrive at a party, and realize I misread the room. I wanted to be noticed but I didn’t want to stand out.

I remember showing up to my first tech job. I started off as a temp, so didn’t quite know what to expect. I sported a gray, slightly oversized suit and maroon checked tie. Seemed appropriate for a corporate environment. When I arrived, I was shown my desk, given a tour of the office, and told never to wear a suit again. Blend into the surroundings. Fit the culture. It was a good lesson to learn. How you show up matters. Context matters. The suit I wore would have been perfect for a bank or an insurance company, but not for a tech startup. From then on I wore jeans or khakis and a button-front shirt. To be taken seriously I had to play the part. To be heard I needed to blend in, as if to say: “Listen to my ideas. I’m one of you.”

These instructions, these rules, have always come from some place. My mother, my geography, my friend group, my coworkers have all contributed. I’ve been influenced by the TV shows and movies I watch. The music I listened to influenced my mood and my color palette. But now those points of reference no longer feel shared. Now I get most of my style cues from Instagram, my algorithm subtly shaping my fashion point of view. It feels both hyper-personalized and hyper-bland. What I see is tailored to what the algorithm believes about me and the millions of other people the algorithm thinks are just like me. Instead of feeling specific it feels homogenized. More uniforms. 

And maybe that’s it. I don’t want to wear a uniform anymore. 

I have no office culture to cue me on how to dress. No audience to dress for. No group to belong to. It’s freeing, but my wardrobe hasn’t yet caught up. I’m sitting at a table on my rooftop wearing a Polo button down and it is beginning to feel constrictive. I’ve tried on a lot of different looks throughout my life, my style shifting with my context and my confidence. What I wore was dictated by where I was going and matched to expectations of who I might find there. Why am I still wearing the same outfit when the room has changed? 

The other day I saw a man walking down 46th Street near 8th. His look was polished but simple. He had a leather tote slung over his shoulder and an emerald green neckerchief peeking out of his chocolate colored dress shirt. He wore dark denim and a mint-colored sport coat. I had no idea where he might be headed, but part of me wanted to go there too.