My Boyfriend Tried to Dress Me for a Week and It Almost Broke Us

When I introduced my partner, Avi, to Amelia’s partner, Spencer, at an event last November, I led with the most important information: “Spencer recently dressed Amelia for a week on Man Repeller!” They shook hands, we all smiled, it was lovely. Months later — a few days ago, in fact — I learned that at that very moment, a thought had crossed Avi’s mind: Wow, sounds like a nightmare.

He offered this insight as we conducted a retrospective on his attempt to dress me for part two of the series. (You’ll notice I used the word “attempt.”) “I fundamentally do not understand how you dress yourself,” he said when I prodded for details. “I don’t know where you divine your inspiration from! I only have two rules: 1) flatter my legs and 2) flatter my ankles. Otherwise, I just wear the same shit over and over.”

In early February, I’d eagerly pitched him as my stylist, assuming he’d think it sounded fun. I was incredulous that he didn’t, so I pressured him into it anyway, because of course it would be fun! Clothes are a hoot! I’m a blast! “It will be so low-key,” I assured him. “Also, you don’t have to do as well as Spencer.”

In a strictly directional sense, it was indeed low-key: the experiment ended with his body curled into the shape of a heap of clothes on the floor of my closet. Kind of poetic. Or in his words, “a catastrophic failure in front of someone whose opinion I respect.” But we’ll get to that in a minute.

Day 1

On the morning of the first day of the challenge, I texted Avi to remind him that after work that day, he’d need to pick my outfit for tomorrow. After replying with three surprised cat emojis and “ahhhh!” there was a five-minute pause and then a shift in tone: “I’m feeling inspired!” Another five-minute pause: “I think this maybe has already gotten out of control…”

I started having what I thought was fun and inspiration, which in hindsight was hubris.

I later learned that when faced with the prospect of actually dressing me, he’d started ticking through his mental Rolodex of style he appreciated and characters that reminded him of me, and then started a mood board via iPhone note, which I only saw later and which he’s agreed to let me paste here, untouched:

Lil Uzi Vert at the Grammys (monochrome, big hoodie, wide leg pants)
Gadget from Rescue Rangers
Bubbles in PPG [Ed note: short for Powerpuff Girls]
Dana Barrett [Ed note: Sigourney Weaver in Ghostbusters]
Drake Hotline Bling meme (red puffer, jordan tee, jeans, boots)
-Kim K, esp her monochrome shit
-ironic take on Patrick Bateman [Ed note: Christian Bale in American Psycho, an inclusion he later justified by saying I’m “the next Bret Easton Ellis.”]
Kendrick in this video?
-Send her emails a la Kanye: “Stop wearing cat-eye glasses, only wear Geordi La Forge visors from now on” [Ed note: a reference to the news story about Kanye emailing Kim that she can’t wear big sunglasses anymore.]

By the time we sat down that evening, he’d zeroed in on Dana Barrett in Ghostbusters for my first look. To my surprise, this process did not start in my closet. He wanted to show me clips of Dana so I could truly understand her character, whom I’d forgotten. Why Dana? Great question. Apparently I reminded him of her for the following reasons, which I took down verbatim in my own iPhone notes:

“She’s a creative, beautiful New York cellist who had a strong influence on the formation of my sexual identity. She’s got kind of big hair, she wears kind of big, thick-looking coats. Definitely some 80s. Lots of houndstooth. She’s very elegant, and obviously that’s in direct contrast to when she’s possessed by Zuul, when she starts to wear off-the-shoulder silky stuff and heavy orange eye makeup or something like that.”

Good American sweatpants, Duggoutt sweater, Converse shoes, H&M coat, vintage scarfGood American sweatpants, Duggoutt sweater, Converse shoes, H&M coat, vintage scarf

We watched a few low-quality clips. None were showing the Dana he remembered from the formation of his sexual identity. He wondered whether we should purchase it to stream so I could get a better sense; I assured him I got the gist and suggested we take a look at my closet. After playing around with various iterations of sneakers and sweatpants under my only houndstooth coat, we settled on the outfit pictured. It was a gentle homage to a look Dana wears home from the gym early in the movie. I felt comfortable but told him it was a little too casual for a workday. He agreed it wasn’t quite right, so we scrapped it and moved on to Patrick Bateman in American Psycho.

After showing me a few YouTube clips of Christian Bale murdering people with axes, he put me in a blue button-down shirt, black pants and black loafers. “I look like I’m sending you off to your first day at an internship,” he said, shaking his head. “It’s all wrong.” You might call this the beginning of the end. We started cycling through his other ideas:

Drake in “Hotline Bling” (too casual, I didn’t look like Drake), Lil Uzi Vert at the Grammys (too boring, I don’t own raver pants), Gadget from Rescue Rangers (I don’t own a purple jumpsuit, am not a chipmunk), Bubbles from Powerpuff Girls (I don’t own a blue dress, am not a bubble). One after another, his ideas went to the graveyard, and the Dana Barrett sparkle in his eye had turned to stone.

“When I started to brainstorm, my fear gave way to a sense of excitement,” he later recalled of making his mood board. “I thought: I’m creative, I’m clever, I spend a dumb amount of time on Instagram. I can synthesize those things into a week of looks! I started having what I thought was fun and inspiration, which in hindsight was hubris.”

About 30 minutes later, he was on the ground, head in hands, and I was no longer laughing. Instead, I was urging him to put me in simple jeans, sneakers and a T-shirt. “A classic!!!!!!!!” I said, with unbelievable enthusiasm. He was apologizing for failing me, but I assured him I knew how he felt: I’m regularly disappointed by how my outfits look in real life compared to how they do in my head. I just wished he felt less pressure than I did; this was supposed to be fun! What’s worse, I too had become self-conscious, wandering into the dangerous idea that somehow I was the problem. Everything was going great. We called it a night.

There Was No Day 2

The next day, I was already laughing about the whole thing but still told him we should kill the story. It wasn’t worth the stress! And it wasn’t worth my sacrificing the comfort I get from dressing myself, either (unhealthfully obtained or not). In exchange for failing his duty as my stylist, though, I asked him to complete the following questionnaire:

1. When did things take a turn for the worse?

“The abrupt transition from carefree to dread/self-loathing came when I started to actually dress you. I couldn’t translate what I had in my head to actual looks, and it immediately eroded my confidence. So what was supposed to be a fun evening with my partner gave way to anxiety. I felt the judgmental eyes of the internet on me as I thrashed about, desperate to re-create Dana Barrett’s Upper-West-Side-post-symphony chic.” [Ed note: Guess it wasn’t post-gym! I’ll be a better film student next time.]

2. How did you feel when you curled up on the floor?

“I felt humbled and defeated by your closet. My only appropriate response as a subordinate was to prostrate myself at the altar of your sweaters and slowly allow myself to be absorbed into your closet like Jack Torrance and The Overlook at the end of The Shining (spoilers).”

3. What did you learn from this experience?

“I got a bit more insight into how you get dressed and how much thought you put into your looks daily. I gained even more respect for the alchemy you perform every morning. It helped me look outside my own routine, which involves getting dressed in the same clothing every day like a cartoon. I also had a visceral lesson in the paradox of choice and have a newfound appreciation for the Dewey Decimal System and really all organizational techniques.”

In the tense moments that preceded my begging him to put me in something basic, Avi looked up at me and asked, “How do you do this every day?” I’d never seen him look so earnest. I told him I had no idea, and it’s true: I often feel mystified about how to dress myself, and I’ve been doing it for almost three decades. Perhaps that’s what makes fashion so endlessly compelling to me: It’s a puzzle I have yet to figure out with consistency. In that way, I found his defeat oddly validating. There is an alchemy to clothes feeling “right,” and anyone in pursuit of that knows all about the closet breakdown. Guess we have a new member of the club.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

More from Archive