I Let My Boyfriend Dress Me for a Week

I can name a number of fun stress tests for your romantic relationship.

You two can go to IKEA to test your emotional endurance. You guys can get lost while driving in a city with lots of one-way streets and restrictions on turns to test your conflict resolution skills. One of you can get food poisoning while the other has a cold to test compassion. To test trust, you can ask your partner to dress you for a week.

I asked mine to dress me for the sake of a story. I was trying to find a casual, low-key way to let the world know I had a boyfriend and this seemed the obvious solution. What I thought I’d get were six days of meta-vicarious dressing: that he’d put me in a combination of the wackier, more fun “fashion” stuff I tend to relegate to the back and side corners of my closet until an opportunity permits and the sexier stuff I don’t always have the guts to wear, because where am I even trying to go?

Seven years in this industry has led me to accrue some real star-spangled snazzers, but I rarely wear them. I’m too practical. I hate to be uncomfortable, overdressed, overheated or cold. I have a strong, deep-rooted equestrian aesthetic that keeps me on the straight and narrow. Embracing it feels like home, but part of why I find styling stories for Man Repeller cathartic is because I can dress all the other personalities in my head. I can be so boring when it comes to my own clothes.

Looking into someone else’s closet has the same appeal of eyeing your partner’s meal. It’s magically more appetizing than your own. I hoped my boyfriend would open my closet doors to reveal all the things I secretly want to wear at once and go, “Holy shit! There is giant yellow faux-fur coat and a pair of red cowboy boots in here! Hand me a pair of underwear! Bingo!”

I prayed for it.

Instead, it turns out that my boyfriend, who I am not at liberty to name (he’s not a celebrity or Voldemort, he’s just not “an internet person”), has impressive taste. Halfway through, Leandra said she preferred his style to mine. All outfits he crafted were appraised by various fashion industry friends. It was an event-and-meeting heavy week; his looks got a lot of face time. I’d call the overwhelming majority of response “aggressively positive,” and when I asked each person what it was they liked, many noted his attention to color-coordinating. Straight men, I’ll go out on a limb and generalize, have internalized that shoes must match belt must match watch — and I think that kind of put-together intentionality is really having a “thing” in fashion post-90s grunge redux, which the public responded to.

The process itself was like a sartorial trust fall. I had no idea how scary it was to hand the keys to your wardrobe over to someone else and couldn’t predict how vulnerable it would make me feel. A person’s individual organizational system is a very private thing! More than that, I had to trust he’d pick something wearable, work-in-able, professional, that I liked, that I felt comfortable in, secret hopes aside. We agreed I would tell him my day’s schedule, but that I couldn’t chime in otherwise unless he asked for help. “Do you have [insert kind of item here]?” was the only question he asked throughout. (According to him, I am missing a red suede skirt in a very specific shape — sort of like an A-line tube, if that’s possible.)

Meanwhile, he had to trust that I’d wear what he picked out. Most mornings I wasn’t there for his creative process. He worked without supervision while I was at the gym and laid the outfits out (!!!!! I know !!!!) on my bed, accessories and all.

Of all the outfits he put together — my approval rating of his week’s worth of styling an ascending line from first look to final — I loved the last outfit the most. It was designated for my family’s Thanksgiving dinner with consideration for stuffing consumption, so note that extra points were awarded. The Diamonds are a casual dining bunch, no festive attire required to attend the table. I take advantage of this rule often by showing up to holiday meals in not-the-cool-kind of athleisure. On this day, however, I surprised everyone by wearing a plaid ankle-length skirt and an open-back navy turtleneck with kitten heels thanks to my nameless partner. Can you imagine? It brought the house down. I felt like the favorite child; he got the people’s choice award.

What I learned is that my boyfriend knows me well. Some of these outfits were reminiscent of things I’ve worn before, but tidier, more coordinated, more formal iterations with accessories I likely wouldn’t have picked out. His choices made me realize just how much of a crutch jeans are for me, and how nice it was to try something new. It also never fails to shock me how differently people respond when you wear heels versus flats, as though it’s a sign you mean business. Per him, in addition to not owning enough “pants-pants,” I have abused leopard, could use more color, should not worry about what day of the week it is when it comes to dressing up and could stand to think more about how to “match” my clothes to my hair.

No arguments. Which is surprising, I guess, but it means the relationship stress test worked. Onward, then! To IKEA we go.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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