So You Have a Job Interview This Morning and A Date Tonight, What do You Wear?

Getting dressed is hard — so is committing to a mood as projected by your outfit. This is chiefly because if you’re the kind of dresser who truly appreciates, say, some feckless fringe, or a multi-tiered Flamenco-style skirt, who’s to say that just because you’ve elected to wear one of the two cited offerings, you’re willing to be typecast as she who is ready to rap battle ye old Western way or salsa dance like no digital emoji has ever danced before? Said accoutrements could frankly just be functioning as band-aids to assuage a good mood handicap.

And when you’re trying to evince several different vibes in one outfit, the game of dress-up gets even more confusing. Case in point: an e-mail I received from my friend last week requesting help with constructing the right outfit for a day that would include a. a job interview at a new fashion start-up in the afternoon and b. a super duper hot tamale rawr, let-me-roll-my-r’s date by nightfall. These two events would cushion the larger event of the rest of her day which is, you know, her current job in advertising.

I thought about what she should wear taking into account that the interview outfit had to elicit this sense of, “I have my shit together,” while the date outfit should have theoretically evoked the spirit of someone who can let her hair down freely, to flow like apple juice in a kindergarten class and stream like a river full of hyperbolic metaphor. She’s also not allowed to wear jeans to work which of course made my immediate and instinctive suggestion — high waist, flare leg jeans and a silk camisole + cardigan to take off later IF YOU KNOW WHAT I’M SAYING — null and void.

In continuing to mentally construct the outfit, I figured that she might be best suited to wear a pair of ivory trousers that fit slightly slouchy but still maintain the silhouette of her legs with a grey crew neck sweater over a white muscle tank (she will lose the sweater for her date), paired with loafers for the day (which say, “I’m confident enough to stand off heels and smart enough to know that you’d be an idiot not to hire me because I opted for flat shoes for this interview”) which she could conceivably keep on through the duration of her date (for the same reason, basically). But should she want to wear heels, that’s fine too; a pair of strappy somethings to highlight the pants’ slouch would work.

As for handbag? Something small. Because nothing says “my baggage is a carry-on” quite like, you know, a minute carry-on.

Also: consider a selection of dainty-ass-but-cute gold necklaces and a wrist of thick bangles for…uh…posterity.

Do you find yourself in a similar dilemma? Was this helpful? Do you want more outfit advice? TELL ME FOR WHAT. I WILL SERVE IT TO YOU ON A NONREFUNDABLE SILVER PLATTER.

— Leandra Medine