Outfits I’ve Worn in Wildly Ridiculous Situations

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Of all the fictions touted in traditional glossy women’s magazines, my favorite has always been the “Day-to-Night” column. You know, the one where your flawless professional work outfit transforms, thanks to application of a darker lipstick and larger earrings, into a dazzling cocktail or first-date look. Has that ever actually happened? Are some human people actually able to go from gym to work to cocktails and have their hair and makeup and overall garment situation not even a little rumpled?

Part of the mystery is because I live in New York City, the land of the fashionable packmule. Unlike my friends in other cities who have the luxury of driving to work in mobile closets (or “cars,” I’ve heard them called), I leave the house every morning laden not just with a purse, but also an increasingly dingy tote bag stuffed with lunch, breakfast, a water bottle, a change of shoes, a book, and whatever clothing options I might need for after-work fun and/or the gym.

There’s no going back to my apartment once I’m out for the day, except on those occasions when I lure friends to meet up at the bar that’s a block away from where I live. God help you if you’re in a relationship with someone in another neighborhood — that means double the packing: day-to-night-to-day-again. Throw into the mix the fact that New York is a place of surprise happenings — random pop-ups, day-of invitations to dinner parties, running into a group of friends on their way to a boat that’s also a bar — and I have often run into situations that seem like the Olympics of outfit conversion.

Meeting New Boyfriend’s Parents to Art Rave

Sometime in late 2013, when I was working as an entertainment reporter, I caught an invitation to cover a mysterious warehouse concert featuring both Lady Gaga and Jeff Koons. Unfortunately, it was also the night that I was scheduled to meet the parents of the boy I had recently started seeing at a fancy restaurant, meaning that I would ideally go from looking like a presentable girlfriend candidate to someone not totally out of place at a rave themed around giant wiener dog balloon sculptures. Silk shell tops, as every InStyle piece I frantically Googled for advice, did not seem to be in order.

Outfit Solution: Color-blocked bodycon dress (it was 2013, okay?) with outrageously enormous necklace, frantically applied winged eyeliner in the bathroom of the ferry that took us to the rave, Warby Parker monocle hidden in purse.

Office to Bar Opening Where Bill Murray Serves Tequila to Cat Wedding

One of my friends in LA alleges that sometimes I speak full sentences that sound like rejected lines from Bill Hader’s Stefon character. (But New York’s hottest doughnut shop really did open in a carwash beside the river!) Usually I protest, but one night — when I went to the opening of Bill Murray’s son’s new restaurant, with the man himself serving shots of tequila, followed by my lovely former coworkers’ housewarming/cat wedding — did actually sound like a shitty SNL sketch. What do you even wear to a cat wedding? Feline formal? Cocktail whimsy? What about to see Bill Murray bartend at the packed opening of his son’s new restaurant? Basically a giant shirt with his face on it, right?

Outfit Solution: Honestly, I don’t even remember — I think I panicked and wore a blue swing skirt and a black top and some jaunty new sandals. Buckley and Paula made a very happy cat couple, though.

Industrial Kitchen to Office to Yankees Game

One of the joys of my job at a food website is often I get to eat and make delicious things. The hitch is that industrial kitchens, in my experience, are often hot, loud places that require hairnets and aprons, or, you know, an acceptance that you’re going to be covered in flour. On this particular day, I had a meeting at a bakery where regular business casual doesn’t work so well. Then I had regular hours in front of a computer at my office, followed by a Yankees game, to which a pal of mine had offered last-minute tickets.

Outfit Solution: Universal Standard black dress, Keds, bike shorts underneath to avoid bleachers-climbing accidents.

Dog Show to Literary Leftist Valentine’s Day Party to Soul Night at a Bar

The Westminster Dog Show is the most wonderful time of the year, and my favorite New York holiday. Did you know you can buy a ticket and go even though you’re just a plebian member of the dog-loving public instead of an expert or whatever? You can. Anyway, hot off a breakup one year, I decided to go the extra mile and attend three events in very different corners of New York: the agility competition, an annual party held by a radical publishing imprint, and a dance party at a bar. Bonus: It was Valentine’s Day. Double bonus: The temperature was in the teens, with a heavy carpeting of snow on the ground. Triple bonus: The party gave you a 50 percent discount on drinks if you wore red.

Outfit Solution: Black tights, beat-up but waterproof cowboy boots, tights, enormous puffer jacket of despair, woolen circle scarf I made while in breakup despair, black shift dress. I brought a red-and-black dress along in a tote bag that I shimmied into in the bathroom of a bar. Hastily applied eyeliner, as always, and a flask that had Loretta Lynn lyrics engraved on it that I subsequently lost (RIP).