I Let My Boyfriend Dress Me For an Entire Year

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[Content Warning: This story contains discussions of eating disorders.]

About a year ago, I turned to the man I had just started dating, and as one so often does at the beginning of a relationship, I said something completely insane. “You have such great taste. Do you want to give me tips for dressing better?”

Perhaps asking your lover to do something most succinctly referred to as “Kim and Kanye-ing” you is an obvious mistake. But it was true—my sweetheart did have great taste. He cared about what he wore and knew how to sew. He owned Gucci shoes, Dries Van Noten Shirts, and Missoni towels nicer than most of my clothes. He was a working artist described by one gallery as the “Master of Color,” whereas I could not be trusted to judge if any two colors go together, unless those colors were “black” and “slightly lighter black.” When I told a female friend about my sweetheart’s sartorial style and his impeccably decorated house, my friend remarked that his taste probably rubbed off from his ex-girlfriend. “It’s the opposite, actually,” he told me when I repeated the theory. “She got her style from me.”

Because I had long been struggling with the fact that I was, in fact, interested in women’s fashion but wasn’t, in fact, able to execute a coherent outfit, I blurted out my little cry for help. Luckily, he thought it sounded fun. He agreed.

Almost immediately, I was shocked at how much the whole experiment hurt my feelings.

Essentially, we started from the place where any romcom heroine starts before her makeover. On the day I asked my lover to style me, I would have said that I didn’t dress for men and I didn’t dress for other women; I mostly dressed for the weather. I could see any photo of Kristen Stewart walking around town and feel that yes, this is what I wanted to look like. What I lacked was the understanding of how to put on my boxy crop tops and ripped jeans and feel maximally fashionable, or maximally beautiful. Usually I felt maximally like a teen skateboarder.

At first, the suggestions my lover made were just funny. Right away he told me that I should be wearing much tighter clothes, sporting necklines that showed off my boobs, and dressing in brighter colors—that I should be, essentially, more gender-conforming. I told this to a female friend, who sighed, “I’ve run that experiment before with men: ‘Be my stylist! What do you like seeing me in?’ And the result is always, always being sexualized.” I had hoped for high fashion (strange knits, elegant linens, statement…. vests, I don’t know!), not “How To Be A Pretty Lady 101.” But he was, after all, my lover—a man personally invested in the fact of me being a pretty lady—and he kept telling me that one day, I would come to regret not showing off my body more when I was young and hot.

He was right, of course. I knew he was right. I knew that Nora Ephron quote about wishing she’d worn a bikini from the entire time she was 26 until she turned 34. I was firmly in my bikini years, and I appreciated his help in taking advantage of that. One day we were lounging in bed, him in his pajama outfit of a mint green Nike athleisure suit, me in the highest-waisted, fullest-coverage underwear you’ve ever seen on God’s green earth. He folded the waistline of my underwear down over and over until they were low slung, then hiked up the fabric covering my butt. “There,” he said. “This is how it’s supposed to look.”

I took his note. I bought some thongs.

I realized that I did want to be desired, especially by my lover, so I started dressing sexier. I liked how I looked and so did he, and the whole experience genuinely made me feel very hot. I loved to walk around stores with him—trying things on, knowing that he was thinking about what would look good on my body, knowing that he saw my beauty and appreciated it. “Covering my naked body in clothes” is a daily part of my existence, but until then, I had never been able to deeply discuss that with someone whose relationship to my naked body was “a big fan.” We walked around Salvation Army buying jeans that actually fit me at six sizes smaller than I thought I wore—a moment of true shock. We swapped links to cute clothes and DM’d each other whenever one of our favorite musicians, a woman who looked like me, took a mirror selfie—this could look really good on you, he would say, under a photo of her in a crop top and tennis skirt.

But of course the whole thing made me feel shitty, too. Every time I threw on my beloved wide-leg jeans or any of the clothes I got as hand-me-downs from a friend a foot taller than me or from my male cousin (this accounts for 80% of my clothes), my lover would tell me that the outfit wasn’t doing anything for me. If I’m such a hag, why did you even start dating me? I would wonder. My lover made it clear to me that he thought I had a hot body, and he knew of some conventional sexy lady ways for me to communicate that, but I felt like he didn’t understand that I didn’t want to be hot in a sexy lady kind of way—I wanted to be hot in a “Patti Smith living in the Chelsea Hotel secretly having incredible boobs” kind of way. Talking to my lover about how I could dress sexy, respect my giant brains and human worth, and communicate who I am sometimes felt like negotiating with the patriarchy in real time. I worried that what I was doing was wildly anti-feminist, like falling into a sexist mentor-neophyte role. Was this whole thing Pygmalion if Pygmalion loved Gucci and Pygmalion’s statue was sometimes an annoying bitch? Had I never asked a female friend to style me because I only valued men’s opinions, or because it was very intimate to ask someone to think so deeply about how your body is perceived (and also just a big time commitment)?

My worry that I was actively harming the feminist cause with my little makeover extended to the fact of just how small these pants I was trying on were, and my emotional reaction to seeing the sizes that now fit on my body. Like many people who have been exposed to the chaotic, violent guidelines we call “the Western beauty standard,” I struggled with eating disorders during my late teens and early twenties. I’ve been healthy for years now and my body has returned to its set level, but it happened so slowly and I’m such a cheap bitch that I never went out and bought new clothes to account for my changed body. (“Oh no, my oversized shirts are now oversized-er.”)

And then, all of a sudden, I was in a dressing room fitting into a dress in size “conventionally hot woman of the early 2000s.” Seeing how my slimmer body looked in these clothes made me feel really good, and the fact that it made me feel really good made me feel really bad. I wondered if I’d relapsed and somehow wasn’t aware. I ran this nebulous sense of unease past my lover, who had no idea why I was so freaked out. I decided I wasn’t suffering from an eating disorder (my new stress coping mechanism is “calling my boyfriend to complain about literally anything”), but realized I associated wanting to look hot to others with being in a bad mental place and punishing my body—so it was strange to intentionally look hot to others, as a healthy adult.

My “styled by my lover” experiment was complicated by the fact that I am a Millennial and my sweetheart was a Gen X-er. My older male lover wants me to show off my boobs more. Florals, for spring? Groundbreaking! His age also meant he thought that some of my fashion choices were hideous when I knew that they were, in fact, hip with the kids. My lover was not a fan of my wide-leg pants, and he was not convinced when I told him that skinny jeans were out and wide-leg was the style now. (Though, to be fair, as someone who primarily watches TikToks on Instagram stories, if I know about a style, it’s probably already on its way out.) Even worse was when I parted my hair in the center. “It looks bad on you!” he told me.

“Gen Z makes fun of Millennials for parting their hair on the side!” I shot back. Eventually we reached a detente; he started referring to my center part as my “away from my boyfriend hair.”

The experiment was also complicated by the fact that some of the things he suggested I do—like wear my hair half-up or wear hoop earrings—looked a lot like how his ex dressed. I wondered if he thought those things were hot because of her, or if she wore those things because he suggested it. I wondered if I even had the right to wonder, because here I was, Kim Novak essentially asking to be Vertigo’d (spoiler).

Slowly, though, the way I dressed changed. My pants got tighter; my clothes got more colorful. My lover suggested I buy a vintage pair of magenta corduroys, pants I never would have even pulled off the rack, and I was shocked to discover how much I enjoyed wearing them with tight, clashing orange or lilac crop tops. I realized that when I wore pants that fit, they felt uncomfortable not because they were too small, but because I was letting the general public see the shape of my body, even though they did not deserve to. I took the suggestions that resonated with me, while using the ones that didn’t resonate to realize, finally, that I did have taste. There was a reason I was wearing a lot of the things I wore—I was doing it on purpose. All it took to realize was getting into a disagreement with someone about why, actually, I do want to keep wearing these wide-leg jeans until my perfect ass rips a hole right through them. And then I would buy the exact same pair, but this time in a size that actually fit me.

I highly recommend being a woman who talks to a male lover about female fashion. It gave him and I a project, a whole new sphere of things to discuss. While at times I couldn’t believe I had created a relationship dynamic in which I was constantly being undermined (I never got full-throated compliments, only general appreciation with a side of, “Are these the only sunglasses we’re working with?”), eventually I learned to see the critiques for what they really were: love, in the form of thoughtful attention. It felt so novel to walk through a women’s clothing store with a man, referencing a tweet about how women these days have two fashion options, milkmaid or ‘90s rave slut, and to look at dresses together whispering, “Milkmaid. Milkmaid. Milkmaid.” It felt intimate and adult to invite him into a dressing room with me—not because I was trying to get arrested for fucking in public, but because I was both 100% comfortable with him seeing my boobs and genuinely wanted his sartorial opinion, a combination I had never before experienced. He made me feel wanted, cared about, and considered.

After a year of being styled by my lover, I have thought and talked about fashion more than I ever had in my life, primarily because I talk to my lover more than I talk to anyone else, which is a huge personal failing and my cross to bear. It turned out, I was a woman who dressed for others. My sweetheart made me feel like I was just a hot person with a tendency to get in her own way, and offered me encouragement to dress in a way that would make people desire me. But I also dress to be understood by others and appreciated for who I genuinely am: bookish, comfortable, happy to put on a dress and get my boobs out every once in awhile, but happier on most days to wear massive underwear with my hair parted straight down the middle.

I bought barely any clothes this year and the ingredients of my outfits are basically the same, but now, I find myself reaching for the items in my closet that actually flatter me (including some pieces I’ve loved for years and, in a big “I’m in my 30s” moment, finally had tailored). On most days, in most circumstances, I still see clothes first and foremost as the things that keep my body the correct temperature and allow me to go outside without getting arrested. I’ve realized that most of the time, I don’t care about looking sexy, but on the occasions when I do care, I now know much better how to do it.

I pushed outside my comfort zone and learned to like new things—a disorienting process for a straight woman who doesn’t want to lose herself to a man, but also, I think, an under-appreciated aspect of romantic and sexual relationships. The entire thing was an encapsulation of what it means to date: to want to be wanted, to want to be loved, to do things just because you know it will make your partner happy, and to realize you were just fine before they came along. And of course, to do a whole weird experiment that is definitely stupid, just because it seems like it will be fun. “Doing stupid things just for fun”—if this is not the meaning of life, I don’t know what is.

Months and months after I asked him to help me dress better, my lover DM’d me a mirror selfie from that musician we loved so much, wearing light-wash jeans and a black band t-shirt cut into a tank. She looked like Kristen Stewart getting coffee; she looked incredible. “This fit is probably her most Blythe-y,” my lover wrote. I felt, all at once, desired and seen.

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