I Let My Women Coworkers Dress Me a for a Week—In Their Clothes

“You look really nice today.”

“Sorry, what was that?” I responded. With my headphones in, I assumed I’d misheard what this woman, a complete stranger, had said to me, unprompted, on the streets of New York. I paused my music.

“You look really nice today,” she repeated clearly. “I dig your outfit.”

Startled and suddenly unable to remember my name, much less my attire, I looked down. I was wearing my little sister’s oversized leopard-print sweater. She’d left it at my apartment; it was chilly (and also laundry day) so I decided to rock it. I continued on with my day, and to my surprise the compliments on the sweater rolled in from various parties: my friends at brunch, the waitress at the restaurant, my sister when I sent her a photo. People were really digging it and, better yet, I was digging it — digging me.

This all caught me off guard, though maybe it shouldn't have. Upon reflection, a ton of my favorite clothes are borrowed or stolen from (or at least previously owned by) women in my life. These include my mom’s giant flannel shirt she wore when she was pregnant with me; my mom’s yellow rain slicker that people say makes me look like the Gorton’s Fisherman; my ex’s NASA bomber jacket that I had to return when she left me (thanks for bringing it up); a Gatorade hat belonging to the wife of my coworker; a different ex’s pair of sparkly socks I tried to return but she insisted I keep when we split (thanks for bringing it up); and of course the aforementioned sweater.

I’ve sort of serendipitously stumbled upon the above items, never gone searching for them. I don’t shop in the women’s section, but whenever I’m at work, I find myself coveting my women coworkers’ outfits. “I just love that color on you!” I’ll say, or “Look at that pattern!” or “Can I borrow that sometime?”

I’ve always meant it but never followed up. Why not? And why do I gravitate towards items worn by women in the first place? And what if I manufactured a reason to actually wear those outfits?

So I recruited a roster of eight very generous and very stylish coworkers who identify as women and represent a diverse array of aesthetics. I invited each of them to dress me for a day... in their clothes. Before we started, I set these ground rules:

1. I get to wear my own shoes. My coworkers were disappointed in the footwear selection I provided to pair with their outfits. I, too, am sorry I don’t own size 10 ½ wedges.
2. I get to wear my own underwear. I didn’t think I had to clarify this, but one coworker (who did not dress me up) asked about — and challenged me on — this particular guideline.
3. The outfit must be work-appropriate. So no-go on that midriff tank.
4. The outfit must be weather-appropriate. So no-go on that midriff tank.
5. The outfit must not be culturally appropriative. Again, didn’t think I had to mention this, but two of my coworkers (who did dress me up) had a big ol’ laugh as they considered putting me in a head wrap and getting me eviscerated by the internet. HA. HA. HA.
6. Try to make me look good. Godspeed.

Here's what happened.

Styled by Michaela

On the first day I wore Michaela’s blue and purple romper with her faux fur vest. How did I feel? Was it like the times my older sister and her friends would tie my blonde curls into pigtails and, much to our mutual delight, put me in a tutu, transforming Benjamin Michael into “Britney Michelle”? Not exactly. Was it like the first (and last) time I tried drag, for a fundraiser in college? Nah.

Heading into work that day, I felt something, but I wasn’t sure what. At that point, I also knew what I wanted to try for this story but no idea what I wanted it to be. I knew I didn’t want it to be some dude-sees-how-hard-it-is-to-walk-in-heels empathy experiment, but I also had no hypothesis on what would happen.

By the end of the day, yes, I happened upon a few of those predictable outcomes, like how, when you wear a romper, it’s super inconvenient to get totally naked to use the bathroom at work.

Styled by Pilar

Pilar dressed me in one of her signature outfits: striped gauchos, a black turtleneck, a scarf, and some cozy wool outerwear. “I just wear a lot of blankets,” she told me.

Writing this story, beyond an opportunity to spend a day in pants whose elegance are only matched by their comfort, was, unexpectedly, another exemplar of (and an opportunity to acknowledge) my own privilege. What I mean to say is, I know this experience would have gone way differently (even dangerously) were I someone who looks different or identifies differently.

I’m fortunate that, during the week, the worst thing that happened was at a pasta place where the guy behind the counter, noticing my outfit before my face called me “ma’am.” He looked mortified — though I wasn’t offended — and said, “Here you are, SIR” as he handed over my to-go bag. I opened it back at the office and found an extra piece of garlic bread — an apology, I assumed.

Styled by Soraya

Soraya adorned me in flowy black capris, a silk floral shirt, and a sleek black jacket. She’d clearly put a lot of thought into the look, and put a lot of trust in me: “Do NOT wash these when you’re done. If they get wet, they’re RUINED.” Pretty cool to have such enthusiastic participation from our brand-new COO, who was also managing me at the time.

I work at DoSomething.org, the largest tech company exclusively for young people and social change. When we’re not dressing each other up, we're activating 6 million young people to donate period products to homeless shelters, clean up cigarette butts, demand gun reform, register to vote, and more.

During the week, I felt especially grateful for my job. Most places wouldn't allow an employee to carry out this kind of story in the office. At DoSomething, meanwhile, even my C-level coworkers eagerly awaited each day’s new look and responded with compliments, critiques, or “Wait! Wait! Don’t tell me!” as they guessed whose outfit I was wearing. I posted a few photos in our Slack; “I’m so mad I’m missing this!” said our CEO, who was out on maternity leave.

DoSomething — the office, the culture, the people — represented a safe space, something I never considered needing. It was a bastion of comfort, positivity, and acceptance. I’ve always defended the importance of safe spaces but, for the first time, could empathize, even in a tiny way, with people from backgrounds and identities who require these kinds of places for solidarity, support and, ultimately, survival.

Styled by Marissa

To be honest, part of me expected to be dressed in clothes that were more outlandish or flamboyant; most days, the outfits weren’t even that far from something I’d wear normally, like Marissa’s choice of denim joggers and a lovely green cardigan adorned with gold buttons.

But even when I walked down the street or rode the train wearing something that was even marginally more conspicuous or “feminine” than my usual outfits, I was suddenly thrust, for the first time, into a world of uncertainty where, even in the progressive metropolis of New York, I wasn’t sure how people would see or treat me, a testament to my own fragility and my newly discovered awareness of it.

Even if strangers noticed or cared, I’m fortunate that my family didn’t; they accepted and encouraged me as always, a constant I realize I sometimes take for granted. My mom, an elementary school counselor in Central Ohio, runs a lunchtime group called Gender Creative Kids for non-binary, trans, and gender non-conforming students and their allies. My dad isn’t so outwardly progressive but, in his typical fashion, added support from a distance: “Fun project,” he told me, and meant it.

At the end of the day, I had family and friends and coworkers who love me regardless of what I wear or how I look.

And as a straight cis white man, I could take off the clothes and feel like myself — feel accepted — while so many others, whether regarding skin color or body type or hair or anatomy, don’t have that luxury. All this is to say, I’m lucky and, even more, I’m learning.

Styled by Karen

“You look lovely,” some said while I was wearing Karen’s biz cas' pants, her blazer, and her turmeric-colored scarf. “And you with that bag? Cute!”

I’m unaccustomed to being described in those terms or as “pretty” or “beautiful,” and I'm certainly unaccustomed to feeling them. It felt good. I found myself wondering, if I can accept and internalize those descriptors, what about other words, other qualities so often ascribed to femininity?

If men give ourselves permission to be and feel “beautiful,” can we also value being “vulnerable” or “expressive” or “gentle” or “tender”? Can we cultivate more “feminine,” more nuanced, truer, better versions of ourselves — for ourselves and within our relationships?

Writing this piece, I found, was a tiny foray into redefining masculinity for myself, an opportunity to reconsider and, in my own small way, begin to rebel against the strictures we’ve created and reified at the intersection of gender, sexuality, and style.

I wonder how I — how we — can challenge other conventions of toxic masculinity and masculinity in general.

I’ve recently been more intentional in my homosocial relationships: talking to my guy friends about breakups; about race; about sexual inadequacy; about our moms; about how we’re personally implicated in #MeToo; about mental illness; about fear and sadness and insecurity and loss. I’ve started showing more affection for the important men in my life: hugging them, holding their hands, kissing them on the cheek. I don’t need to wear a lovely scarf and carry a purse, but I definitely need to tell my dad I love him.

Styled by Alex

Alex had me rock a thrifted Little League baseball jersey, a dad-style hat from SZA’s tour, and a sweatshirt she told me belonged to a friend who’s six-foot-six. I swim in it; she practically sinks. Meanwhile, “how do you fit into those?” a coworker asked about her tiny, tiny jeans.

“Shape-shifting,” is what I offered as a less-than-clever quip, but it might be more accurate than I realized, figuratively speaking, anyway.

There’s that old cliché about walking in someone else’s shoes. How about literally wearing someone else’s clothes? I can’t say wearing a woman’s clothes made me feel like a woman, but I definitely felt… different. Doing a little pirouette and savoring the twirl of my flowy gauchos made me feel more… elegant? Rocking a smart, biz cas' blazer made me feel more... sophisticated? Sporting a hat from SZA’s tour made me feel more… relevant? I was introduced, in small glimpses, to different versions of myself. Then I ran out and bought two more hats like that one.

Styled by Bonnie

On the last day, Bonnie put me in high-waisted jeans, a floral blouse, and a leather vest. One coworker observed that I reminded her of “a sassy mom in the '70s.” And you know what? I kind of felt like one, too; throughout the week, I subconsciously acted and carried myself differently.

The sensation of wearing these clothes felt like expanding my vocabulary or learning a new language — suddenly, unexpectedly being able to more fully express myself or, perhaps, parts of myself I didn’t know existed.

I wonder what other ways I can take little steps to move towards self-actualization, to become a little more fearless and a little more authentic in the way we represent ourselves through style and otherwise.