I Asked Instagram Commenters to Dress Me for a Week and of Course It Got Weird

leandra medine instagram looks man repeller

Last fall, Man Repeller alumna, Amelia Christina Gets Drunk at The Cheesecake Factory Diamond allowed her colleagues to dress her for a week. As it went, each morning one of us would send a text message with a prompt. Then she would hold the mandatory suggestion against the tasks of her calendar and style accordingly. What resulted, in my view, was her simultaneous dexterity as a stylist and a portrait of her genuine commitment, whether unwitting or deliberate, to looking like herself, no matter the circumstance (see: Legend of Zelda picks up her dry cleaning). As a sort of spin-off, last week I tasked myself with the work of asking my Instagram following to dress me for a week.

What resulted was upwards of 1,500 suggestions, deposited by direct message and public comment (with no shortage of genuinely kooky rendering requests), of which I am positive Man Repeller will be able to make use for at least the next, let’s say, year. But I could only pick 5, so I pooled the most common themes–nonsensical marriages of odd couples from opposite ends of a spectrum (see: a quinceañera and Thanksgiving in the South) or the combination of office-attire and effectively anything else–and made up a work week’s worth of outfits to fit the prompts without sacrificing my own style for both your viewing pleasure and my closet’s amusement.

As the great Kevin Costner once said, “If you build it, they will come,” so, prompters, here’s hoping you’re here.

Prompt: “Lingerie but make it business”

The logic: The previous sentence from the prompt read, “You’re a very important businesswoman who slept in late at her partner’s apartment and now has to rush to work.” I assumed it was a Thursday night because it was in my interest to make such an assumption and took creative license/further assumed there is a casual Friday policy at the office, but even if there is not, given that you are an important businesswoman, surely your higher up has to be out of his (probably his) mind to expel you on the account of your machine-friendly, casual poplin. You’re important, after all.

Anyway, for your date, you put on your lightweight wool checkered finest. They hug your butt exactly the way you hope all office garb will. With it, you paired a negligee, essentially. A negligee that would effortlessly collaborate with said machine-friendly poplin. You’ve got files in your bag, and loafers on your feet. In an alternative reality, you wear this to work, shirt tucked in and buttoned up, then let down your hair so to speak, before you’re about to meet someone with whom you hope you’ll have sex. Of all the outfits I assembled, this one feels the most me. Feel free to unpack that.

Prompt: “Britney goes to Walmart”

The logic: The prompter specified the spelling–and she was called Britney. Not Brittany. Brittany may have worn something profoundly different. But Britney, carrier of multiple decades’ worth of public growth and therefore also the plausible recipient of manifold projected personas, is, paradoxically, specific. I chose to marry “the hit-me-baby, but also I can wear a snake, NBD,” Britney to a classic Walmart shopping scenario. The particular Walmart scenario I envisioned featured a busy parent trying to get their kid all the things he or she needs for school before school starts. Cue (I mean kah-yoooooooo) the tote. The latter is reflected in the shorts and the style of shoes. The former, in the rhinestone bralette and souped-up shoe buckles. I hate myself for not getting body rhinestone stickers.

Prompt: “Women’s U.S. soccer team meets Cruel Intentions

The logic: Fo the rare bird who has not seen Cruel Intentions, I invite you to review this Wikipedia rendering of the character I’m emulating from the movie (the original!). The TL;DR is that she ruins people’s lives for fun and more often than not uses sacricities such as sex and religion to do it. Not to beat you over the head with the obvious but that’s why I’m wearing an at-first-glance modest dress that actually exposes all my shit. Meanwhile, soccer players love high socks—high socks and shoes that make running super fast and kicking balls easier. Whoa, it just occurred to me that a female soccer player is a special kind of hero. She literally kicks balls that she doesn’t want in her court, out of her court for a living, but I digress. I’m wearing high socks and sneakers to commemorate Her. Could I be a Danish influencer? Yeah. Am I frustrated about it? Not in the least.

Prompt: “Recently divorced bee-keeper going to her friend’s gallery opening”

The logic: Here’s this recently divorced woman, vulnerable as fuck (so much so that she has *removed* the net from her hat), trying to find herself again and using social opportunities, like a close friend’s gallery opening, to do it. She walks into her closet and asks herself: when’s the last time I felt like an anchored me? She gravitates toward the panoply of prints that have been relegated to a “maybe I’ll wear this again later” section in her closet. Then, she asks, what would I wear to an art party? Renderings of stiff poplin blouses and wide leg, airy pants come up. She recalls a pair of printed pants. Silk, to be sure! And pairs them with what feels like the most adult-but-still-her blouse she’s got. Ready for a night on the town–a new life on it, in fact. Let’s tango!

And for my final trick?

Prompt: “Mr. Big x Aidan”

The logic: It ain’t a Man Repeller story if Sex and the City doesn’t weave itself in somehow. Amalie (our social media editor and resident poet) recently told me that she watched the whole series after accepting our job offer. The whole series! What would Aidan look like if he was also Big? What would Big look like if he was also Aidan? As I reflect on the answer to this question, it seems I probably should have just tried to recreate an iconic look of Carrie’s. Isn’t she, after all, the amalgam of them both? But that’s not where I went. Instead, I heard Samantha’s voice talking about turquoise rings (and landed upon silver; Aidan would never wear gold, lest it matched some tobacco suede he was wearing), and remembered that there was an encounter in Morocco (see: the caftan). Then I assigned mad stereotypes to the air of the BIZNESS MAN in the S-class Benz-big. Shiny black loafers. Pressed trousers. And, if he was a woman, 10/10 would wear red lipstick. No?

Allow me to answer with: abso-fucking-lutely.

Photos by Sabrina Santiago.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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