I Let My Boyfriend Dress Me for a Week

He was instructed to stick to the rule of choosing what he found me most attractive in.
Publish date:
February 25, 2015
relationships, clothes, Dating, fashion, style, love

My boyfriend and I are about to move across the country from each other, and we’ve decided to do so without continuing on in a long-distance relationship. We care so much for each other, and we’re best friends, so I have no doubt that this will be weird and very difficult, but mostly amicable.

This is the tl;dr on what brings us to laying in his bed at 4 a.m., joking about how strange it’s going to be transitioning from being a couple to being friends (xoJane readers, I can only imagine the “oh, girl” reactions y’all are having right now).

“Okay, now that we’re going to be friends, we can be completely honest with each other about things we weren’t before,” Luke said. “You know, I was never the biggest fan of those black shorts you wore a lot.” He said this jokingly as I felt quick, hot rage crawling up my spine.

“What the fuck are you talking about?” I said to him as this conversation went from zero to 100, real quick. “Those shorts are great and they are classic, and I wear them all the time because I feel HOT in them.”

(Actually, they’re just black, cotton Gap shorts — nothing too special — but I had viewed them as a classy staple.)

I’ll be the first to say it — I dress for men. I also dress for myself, which is why I favor thick hoop earrings, Rod Stewart tour shirts, and lots of leopard print, but I always base my choices on the question, "Do I look hot?" When I dress, I typically have one short, tight item of clothing on with this in mind. For better or worse, I feel at my most attractive while wearing things with conventionally sexy, bodycon silhouettes.

I asked Luke what he finds me most attractive in. He’s afraid to answer this, rightfully, as it resulted in tears the last time we played this game. “I like it when you dress casually in things that aren’t that complicated because it shows off your body more,” he tells me. “Also things that show off your ass.”

I thought I had red-blooded, heterosexual dudes mostly figured out as far as what they think girls look most attractive in because I’ve spent a few years as an observant young female. I was curious to put this to the test. What would he pick out for me? For one week, I gave up the reins of my closet to him — my new stylist.

I think he thought this was some sort of weird mind game I was playing with him as punishment for insulting my favorite shorts, but he went along with it. A little background on my boyfriend: He’s a writer who likes rap music, sports, and video — the thinking man’s bro. He usually opts for old Hawaiian shirts, button-ups, jeans, and fly kicks. His style philosophy? He takes a second. “I’m post-style.”

Day 1

As we were standing in front of my closet that Monday, he was very tempted to pick out what would make us laugh the hardest, but he was instructed to stick to the rule of choosing what he found me most attractive in.

He settled on a forest green Madewell skirt, a baggy, black cotton H&M shirt, and a leopard print cardigan procured from the mom section at Goodwill. It was a somewhat conservative, vaguely school librarian choice. I was pleasantly surprised that he was (perhaps unwittingly) playing around with colors and prints.

This outfit garnered approving stares in my somewhat traditional, suburban office. I thought this was all in my head, but then I got some admiring comments in the break room. Luke told me that he chose this look because it is “cool, cute, and flirty.” Simple enough. The outfit for day one was probably the most traditionally fashionable of the bunch.

Day 2

On day two things got weird — an old L.A. Gear shirt that I got at a thrift store, a pair of skinny Levi’s that, as my friend Alex describes, “look like a storm hit my legs,” and a jean jacket. I was kind of embarrassed to walk into work.

I’m at my desk on day two when a coworker says “Hey, I love your pants!” Preemptively I launch into an explanation of “Oh, this outfit? Well my boyfriend’s dressing me for a week . . .” She stops and says, “No, I love it, I totally noticed something different about you. I saw you in yesterday’s outfit and was like ‘Hmm, something new is going on!’”

I am simultaneously flattered and also now uncertain of anything I’ve worn ever. The outfits I’ve worn the past two days have garnered more compliments than any look I’ve put together for the last month. I tell Luke that people are noticing and he isn’t surprised. “I think it’s just cute and fun stuff,” he shrugs, and that is that.

Day 3

Day three’s look has me feeling mad unattractive. I live in Austin, Texas, which means it’s somehow both chilly and humid, and I’m dressed like a teen boy. I’m wearing a pair of very old Aéropostale jeans, Luke’s New Order shirt (I’m an emotional teen boy), and a black and white herringbone coat I found ages ago at a thrift shop.

Today, I’m going to dinner with my family, and I know I can trust my 18-year-old sister to give me her honest opinion. She smirks, and everything I’ve suspected about this outfit is confirmed. I’m not high maintenance, but I’ve also never really been a jeans and shirt kind of gal.

I have anxieties surrounding ill-fitting jeans, as someone who, completely inexplicably, spent most of high school wearing Gap trousers four sizes too big. I was called out on this in a high school locker room, and now am too traumatized to wear pants that don’t adhere very closely to my ass. High school never dies.

I interview Luke about my wardrobe basics, and I’m appalled to find out that he doesn’t actually like the leggings I wear that much. “They’re complicated.” he tells me. This makes no sense.

“I don’t know,” he explains, “They abstract your body because they’re normally worn with something baggy over them. Jeans are simple and have buttons.” I am still mystified.

Day 4

I’m feeling pretty good about day four because he’s picked out one of my favorite items, my Stone Cold Steve Austin Christmas sweatshirt, and my high-waisted black H&M jeans. This sweatshirt makes me feel like a million bucks because I love pro wrestling and conversational wardrobe pieces. It’s maybe the best 1 a.m. online shopping purchase I’ve made.

Sadly, no one asks me about this sweatshirt because most people don’t care about pro wrestling. In spite of this, I have a damn good day representing Stone Cold. I’m also realizing why I’m feeling in good spirits and, somehow, eliciting some admiring comments about this week’s wardrobe choices. I love fashion because I am a shy person. I will not only bend over backward in order to avoid making someone feel uncomfortable or confronted in any way, I will twist myself into a pretzel with a giant, eager smile.

Fashion allows me to explain who I actually am without saying a thing. Lately I’ve been forgetting to do that. I haven’t been feeling very comfortable with my body because of a busy schedule and a sedentary desk job, and I’ve been anxious over pending important life decisions. As a result, I’ve been very safe in what I’ve been choosing to wear. There have been a lot of the same blacks, grays, and button-ups in my life. I’ve been looking like someone trying her hardest to have Good Taste.

Day 5

My final look resulted in what is perhaps my favorite anecdote from the week. My last outfit was a San Diego Chargers jersey, a yellow pencil skirt I’ve sent some sexts in, and a really fucking fantastic white rabbit fur coat that presented itself like a phoenix at a vintage boutique a few weeks ago.

I was at the grocery store that evening purchasing a pound of gummy bears for my wild Friday night. My outfit had already received some polite stares walking in. The cashier was a middle-aged Russian woman with lovely pigtail braids. She looked amused when I walked up.

“This is really too much to pay for these gummy bears,” she said, seeming vaguely disappointed in either me or the price of Haribo these days.

“I know,” I said solemnly.

“These gummy bears are not worth it,” she said, then, making pointed eye contact with me, she said, “But you are worth it.”

Later that night, I wore this look for a very chill kick back at Luke’s apartment. I ate too many gummy bears, and felt very nauseous. My friend Andy told me I looked like an extra in a Cam’ron video. No higher compliment has been paid to me. All in all, a very fitting evening for a very haphazard look.

Luke has told me to make it very clear in this piece that he has absolutely no idea what he’s talking about when it comes to women’s fashion. I think, in spite of this, that he has done a pretty good job. I will also say that these five outfits, collectively, probably took him about five minutes to pick out.

Giving up the reins to my wardrobe for a week turned out to be more freeing than terrifying, which was somewhat surprising considering I’m currently going through my 25th birthday-induced crisis over “Oh shit, how much longer can I wear crop-tops and teenage stuff and not look like a try-hard.”

I’m happy to be dressing myself again. But this week? I’m breaking out my dumbest, most fun stuff because sometimes how I see myself is a little bit harsher, a little more in stark relief, than how the rest of the world sees me