I Let My Colleagues Dress Me for a Week and Things Got Weird

All I ever want is a tidy dress code to follow. I blame it on the 10 or so years I spent adhering to a uniform in pre-collegiate school — even though then, of course, I’d do anything including extra credit just to get a “free dress day.” Now, I’ll do anything to have someone else tell me what to wear. Weddings, cocktail parties, your aunt’s birthday, a standard Tuesday dinner: I will ask you if there are any guidelines or hidden physical activities in the pipeline (“Will we go dancing or napping after?”) that might help narrow my shoe selection.

Part of me likes to think it’s because dress codes make dressing easier, but that’s not always true, is it? Some can be boring. Others, archaic and stuffy. Plenty are unhelpful at best! Raise your hand if you’ve ever been invited to wear “cocktail casual with a wintry flair” or something simultaneously vague and esoteric that makes you want to call the host to ask, “Love the font you used on the Paperless Post, but please, for the love punctuality, is this finally the time and place for my massive marabou tutu, or what? Please clarify!”

The dress codes I like are those that help me scribble within the lines. Rather than be over- or underdressed, I prefer to know constitutes as “appropriate” so that I can use the rules to help me expand my imagination without feeling overwhelmed by a too-vast world of “wear whatever” options.

And so, drunk on the allure of daily dress codes, I handed over the reins of my wardrobe to Harling, Nora, Leandra, Haley and Emma. Their duty: to give me one new dress code every day for a week. With no access to my actual closet beyond their respective knowledge of what I tend to wear, the only real tools they were equipped with was access to my schedule.

Did it make my life easier, my outfits more creative, my mornings more efficient? Or did it, on one day at least, cause me to look like an 1880’s schoolmarm in a bucolic story setting? So glad you asked…

Day 1. Stylist: Harling Ross

Main thing on schedule for the day: Styling a photoshoot in Upstate NY. All-day affair.

The result: Harling very kindly dressed me almost exactly how I would have dressed myself on this kind of day — only for sure a bit nicer/cooler. I don’t think about my own outfits on serious shoot days like this. I think first and foremost about my comfort, well-knowing that I’ll be on my feet, schlepping things, holding a lot of stuff with my mouth while my hands are busy, and alternating more rapidly than usual between feeling too hot and too cold. Shoots are about how the pictures look, not how I look.

But! I hate feeling “schlubby” as a rule, and Harling’s pretty specific instructions kept me in an outfit that, save for the boots (which I love with my whole heart but tend to keep in an outside-of-NYC context), felt like something I’d wear to the office. There wasn’t too much room for interpretation on this day — a blessing due to my early morning start, but I did add earrings in honor of what I knew Harling would do, and though I arrived in a very old beanie of mine on-set, I swapped it for this navy and black Tibi one the moment I got my hands on it. (It went better with my outfit.) On this day, probably couldn’t have handled much more of that so-called “scribbling” inside the lines I boasted about earlier.

Day 2. Stylist: Nora Taylor

Main thing on schedule for the day: Getting hair done for Emma’s Tangle Teaser story, standard day in office otherwise, drink with friend after work.

Assignment: “Please dress like a combo of two of these three Winonas: Winona Ryder from Edward Scissorhands, Winona Ryder from HeathersWinona Ryder from Stranger Things.

The result: Where to begin. First of all, I chose Winona Ryder from Heathers and Edward Scissorhands, mostly because I feared my Stranger Things Winona would look a lot like my Harling outfit. What you see here is a pretty heavy lean into the interpretation side of this experiment. The black turtleneck and boots were an ode to Heathers Winona, and the dress is supposed to be a combo: kind of 80s-ish a la Heathers, but also similar in color to the off-the-shoulder dress she wears in Scissorhands.

This was the hardest challenge of them all, but I came up with the outfit surprisingly fast. I think it’s because I knew I didn’t have the exact items, so there was no use in going too literal anyway. I never, ever wear this dress even though I always want to, so it was really nice to have a reason that pushed me into it. This is exactly what I mean when I say that dress codes or guidelines help me expand my own way of dressing!

Two unexpected twists, however: One is that there was a blizzard that took trees down in our office’s neighborhood and my own, so attempting to walk in a dress and heeled boots (to meet my friend for drinks, if you recall) was tricky — and I realllly hate to be wet or cold. Sure I could have checked the weather, but where’s the fun in that?

The other twist was actually more of a curl: I had to sit around with my head in a full helmet curlers. For some reason, paired with the dress and the boots and the turtleneck, the effect was that of a Laura Ingles Wilder character. Or Martha Washington. I mean the list really went on, thanks to the team who kept offering up visual references. This, I suppose, is one of the unforeseen consequences — or gifts! — of a dress code that takes you outside your normal realm.

Day 3. Stylist: Leandra Medine Cohen

Main thing on schedule for the day: Therapy, half-day in office, half-day work from home. Cocktail party in the evening.

Assignment: This meets this. So imagine if Zelda had to pick up her dry cleaning.”

The result: This isn’t the first time Leandra has tried to dress me like a character from The Legend of Zelda, only the first time she did so, it was subconscious, if not unintentional. This is the first time I complied, however. The MR Buffet parts were obviously easy to copy. Check and check. So too were the sweater and the boots — a perfect half-in-office, half-remote Friday. The magical elf part was a bit more tricky to “interpret” so I focused on the robin egg blue color of her skirt-shield thingy and matched a sweater to it. I wore red cowboy boots as my elf shoes (it made sense at the time plus I thought, “Red — that’s close enough to pink”), and their pointy toes, a nod to her ears. See how I’m holding the bag? That’s my sword. Finally, I added a ton of sparkly pastel Roxanne Assoulin bracelets and sparkly pastel earrings.

This outfit is (obviously) the least literal of the bunch, but that’s exactly the point I keep trying to make: a dress code, or a set of guidelines, no matter how weird, can truly guide you home.

I changed for the cocktail party, I am so sorry to report.

Day 4. Stylist: Haley Nahman

Main thing on schedule for the day: Free Sunday day, friend’s apartment in the PM — she’s having people over for mulled wine and apps.

Assignment: “Head-to-toe color, can’t be neutral! Plus, you must choose a specific animal that inspired it, and share that inspiration with at least 3 people.”

Mango sweater, unlabeled sweatpants -- similar here, Miu Miu shoes Mango sweater, unlabeled sweatpants -- similar here, Miu Miu shoes

Given that I told two people and saved you as my third, I better start with my animal: the axolotl, obviously. (My hair = the red bits.)

Now, Haley specifically said I can’t be neutral. But then I texted her and reminded her that besides my blue Zelda sweater and red cowboy boots, I basically only own neutrals. So! We compromised with this creamy color which she said was “more unexpected for cold weather.” And far more axolotl!

This was the coziest I’ve felt in forever, from my day of couch lounging to the evening sitting cross-legged on my friend’s floor trying not to spill mulled wine on all the cream-colored me, but more importantly, I would have never, ever, ever put this outfit together without the prompting of Haley’s guidelines.

Day 5. Stylist: Emma Bracy

Main thing on schedule for the day: A standard Monday in the office, having my picture taken for the MR Holiday Buffet edition of Office Apropos, no evening plans.

Assignment: “Today I would like you to dress like…(drum roll, please) your mom in 1992 if she were going fishing.”

The Results: Little does Emma know that my mom’s 1992 fishing aesthetic is a daily aspiration of mine — or maybe she does, which is why she chose this outfit for me.

My mom used to fly fish, so I tried to mimic her rubber waders with my leather pants. These Blundstone boots are perfect for puddle stomping and hikes, so they felt appropriate too. (And given that I had to shoot an outfit for another story on the same day, I wanted to be able to wear these shoes and pants in both shots to make things easier.) The sweater’s a roll neck — very 90s, and the waxed jacket and felt hat, like the boots, felt apropos of the fishing theme.

What I didn’t expect is that this would become my new favorite fall outfit, hat and all.

The day after my final coworker-assigned outfit, I returned back to my normal dressing habits. But it wasn’t the same old wardrobe. Suddenly, it was a world of outfit possibilities — a Narnia in its own right — filled with elves and smiling sea creatures and no less than two different kinds of Winona Rider. All thanks to the dress code.

Amelia Diamond

Amelia Diamond

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

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