Introducing the Night-to-Day Outfit

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When I was 12, the day-to-night outfit meant one thing: sex. I’d read about it — in Cosmo, Elle, etc — and pine for the day when I’d be old enough to wear cute business casual garb to my amazing, high-paying job at a magazine. More specifically, I’d fantasize about the clock hitting five, that magic hour when I’d have the opportunity to transform my Ann Taylor Loft Look into something more fitting of Brass Plum. And I’d wear something sexy from Victoria’s Secret underneath, naturally.

Years of studying women’s mags would teach me how to be an effective Woman™. Part of this meant there would be no crappy biz caj uniform I wouldn’t be able to jimmy rig into a costume befitting a sex pot. The high-waisted, knee length pencil skirt would become bootylicious with the cinch of a belt; The three-quarter sleeve rayon blouse would suddenly hold enormous tits at the undoing of a faux pearl button. I’d look so great that the end of the night would mean I’d get to have sex with a real live boy, probably named Nick.

Younger me couldn’t have imagined the ways in which professional culture would change. I’ve only had one job where I was forced to hide my shoulders with a navy Gap cardigan. Most of my work life, in the media and tech industries, I’ve had no dress code at all. Nevermind that this seems to actively encourage people to dress like shit, the ultimate millennial credo means you’re encouraged to be yourself at all times. Hardly anyone is naturally business casual or formal. Most people "live their truth" in a naked state, but since that’s not acceptable in any office culture, a t-shirt will do.

Even more profound than a changing professional world is a changing cultural one. The day-to-night outfit is essentially meaningless when women go on numerous dates a week and don’t really care what some random guy from Tinder thinks. Most importantly, contemporary women understand that finding a partner or even just getting laid has nothing to do with a Banana Republic shift dress. If only it was that easy.

Contrary to the beliefs peddled by Women’s Magazines™, I’ve never had a problem transforming J Crew loafers into club shoe (full disclosure: I don’t wear J Crew loafers or go to clubs). Instead, the quandary I’ve most frequently found myself in has been transitioning a bodycon dress and missing underwear (a dog ate them) into something appropriate for a rush-hour subway ride home. The tales of these next day nightmares are plenty: My friend once put her contacts in a cup next to the bed and the dude drank them in the middle of the night. (She had to endure the entire work day almost blind).

So, we introduce the Night-to-Day Outfit, a versatile look that works at both at your local meat market at 2 am and the Q1 all-hands the next morning at nine. The key to acing this outfit isn’t shoving an extra clutch or dangly earrings into your tote. It’s about preparing yourself mentally for the opportunity of getting laid, and how you will feel the day after that.

On July 4th of this year — a Monday — Hannah, 23, had a date. She wasn’t sure exactly where the night would take her, but she knew she’d probably end up visiting all the New York City boroughs. She planned to spend the day in Brooklyn, watch the fireworks in Queens with a man friend, and then be at work in Manhattan the following Tuesday. "Rather than shuttling back and forth between boroughs more than strictly necessary, I thought it would be easier to wear the same outfit to my fireworks date and work the next day," Hannah says of her night-to-day-outfit. So, she chose a blue dress with a zipper down the front, which was unzipped for the date and then zipped back up for work the next day.

Amber Rose’s Walk of No Shame has awesomely encouraged flaunting your conquest the morning after, but in a professional context, this practice isn’t so straightforward. Whether or not your employer cares, it can be embarrassing to wear the same thing two days in a row, even worse if it’s sequined. And if you work with mostly men, as I frequently have, there’s the reality that they will comment on your sartorial repeat/perceived promiscuity under the guise of a "joke" (most sexual harassment is just a barrel of laughs!)

EJ Dickson, 27, a sex and relationships editor who once went proudly by the office nickname "skintern" has a relaxed attitude towards office attire. But she thinks the night-to-day outfit is less about avoiding slut-shaming and more about being professional. "I think were I single I'd prob be less concerned about being shamed for my sexual choices (cause fuck that) than having people think I didn't take my job seriously enough to, like, put on flats and a blazer and just get it a lil together," she says. "It wouldn't reflect well on my ability to do my job well and that's something that would really bother me."

Whether or not you feel compelled by either some kind of personal or professional etiquette, the beauty of the night-to-day outfit is that it’s not about the guy. At it’s core it’s about your job. It took me a long time to realize that what bothers me most about the day-to-night outfit as a concept is that the focus is on the probable loser who pretended to own a lion to get you to agree to the date.

So next time you are in this quandry maybe wear jeans so you can borrow one of his shirts the next day. Or maybe say fuck heels, because they will be even unbearable on day two or just go with glasses, because I have now warned you of the dangers of contact lenses in this context. Don’t ever ask yourself how can I look good for him? Ask how can I be most comfortable tomorrow?