Hey Fashion Friend: How Do I Dress for Work Again?

Animation: The Cut

On my first day ever at the Cut, I showed up to the office wearing an outfit that I thought projected authority and good taste. It consisted of a black-and-white polka-dot Comme des Garçons pleated skirt that went down to my ankles and black satin Manolo Blahnik slip-on heels with bows. I’d purchased both of these items secondhand with money I probably didn’t have, and had worn them before to my previous job at Condé Nast, where they went largely unnoticed, which in that context was a good thing.

“Aw, it’s so cute that you dressed up for your first day!” one of my new co-workers cooed when we were introduced. I was mortified. Clearly, I’d misread the room.

In the years since, I’ve dressed relatively casually for the office. So casually, in fact, my work-from-home uniform really hasn’t been all that different during the pandemic, save for the days I wear sweats or pajamas. It’s made returning to the office again pretty anti-climactic, fashion-wise; I just throw on the same jeans and a sweaters that I used to and run out the door. I’ll admit there was a moment where I asked myself: Should I try something new? Maybe this was an opportunity for reinvention. A makeover! But ultimately, I decided that was too much work.

This is just my own personal experience, of course. The way we work and our relationship to it has changed dramatically over the last few years, so it would make sense for office dress codes to change as well. It’s a question so many of you have submitted: What to wear? One Cut reader wrote: “I’m going back to an office after two years of working in sweats — help!” You want to be comfy-yet-professional looking. You want to be able to commute — but maybe not on the subway. Many of you started new jobs remotely, and don’t want to make the same mistake I did when you meet everyone in-person for the first time. Or are starting at a company with a different culture than your previous.

I hear you — but I’m afraid I can’t offer much specific advice because no job is the same, even within the same company. What you wear to work depends on what you do, and who you are as a person. I’m a fashion writer who sits at a computer all day, but I also happen to want to dress like the head of a pasta empire.

Allow me to pose a different question then: What do you want to get out of the office? Maybe you just want to clock in and out, or maybe you want to indulge a certain side of your personality. For me, my goal when I come into work is to interact with my co-workers, and I’ve learned that one of the best, easiest ways to do that is by complimenting them. This isn’t hard; they’re all very stylish. But because office interactions are so fleeting — a brush at the kitchen or on the way to the bathroom — sometimes all you have time for is a “Love your [blank]!” and you just comment on the first thing that catches your eye. What I’m trying to say is: Dress in a way that will allow your co-workers to more easily give you compliments. Throw them some bait! Everybody wins, and who knows, maybe your interaction will turn into a longer conversation about, say, your trip out West where you got those crazy cool cowboy boots.

Accessories are the fastest route to a compliment, in my experience. They’re low-risk for both parties, and if you wear them often enough, they start to become your thing, which can also be helpful in an office environment. (I’m working on becoming a Red Lipstick Person, for example. Like, Oh, that’s Emilia, she wears red lipstick.) A colorful hair clip is a good place to start, or maybe a big chunky gold necklace. Funky blue light glasses are also very 2022. One thing we learned from face masks during the pandemic is how much you can telegraph about yourself with a very small object.

Below are some things I’ve complimented my co-workers on recently that maybe you can try too.

Things I’ve Complimented My Co-workers on Recently

This checker-print hair clip that our features editor wears always catches my eye. She said she saw it in our holiday gift guide, so we’re all influencing each other here. I appreciate the hint of ’90s playfulness it brings to the office.

If you’re someone like me who wears a lot of monochrome, jewelry can help add some flair. I saw our photo director wearing a chunky gold necklace recently and wanted one for myself.

Two of my co-workers wore printed mesh turtlenecks on the first day back at the office, so that means it’s basically a trend. They’re ideal if you have to go somewhere for drinks after work.

Wearing jeans to work can feel too casual sometimes. But a denim shirt? Now that is fash-un.

One of my co-workers was inspired by the recent Commission look book, which proved that New Yorkers can wear cowboy boots too. Between these and denim shirts, the office really is the Wild Wild West.

If you’re not a cowboy boot person, my co-worker on the fashion team also says these boots are comfortable enough to wear all day, and out after work at night.

Everyone is always looking for the perfect work blazer. I recently complimented one of my co-workers over at Vulture for this one because it was excellently oversize. She alerted me to the fact that Theory was having a sale. Teamwork!

This cardigan has been sitting on the back of someone’s desk over by the photo department for some time now, so if you’re the owner and you’re reading this: Love your sweater! Cardigans are a comfy alternative to a blazer, and as this person demonstrated, can be left at your desk for when the air conditioning is too harsh.

I appreciate when people wear “dress shoes” or “dress pants” to the office instead of jeans and sneakers. My co-worker over at the Strategist waltzed in one day wearing these, and he looked ready to get stuff done. I was impressed — even more so when he told me they were custom-fitted to his feet. Okay, boss!

Hey Fashion Friend: How Do I Dress for Work Again?