So You’re Going to a Dinner Party at A New Male Friend’s Apartment, What Do You Wear?

Say you just met a guy through a friend of a friend who didn’t necessarily believe you should meet under the pretense of dating, but instead because you maintain similar interests, are both awesome, and should effectively just know each other, right?

So you meet, and as the third party friends suggested you would, you get along. You like each other. Your interests are similar, you are both capable of understanding that the other is awesome and because this meeting wasn’t a date, there is absolutely no pressure on it.

You’re not quite sure if he likes you likes you and to be fair, you don’t know if you felt a connection as friends or more-than either. He invites you to a dinner party he is hosting at his home the weekend post-encounter and naturally, you’re eager to go. But what do you wear, right? It’s a dinner, with people you presumably don’t know, and it’s definitely not a date, but you’d like to appear presentable.

An element of denim will always, under any circumstance, connote your understanding that where you’re going in the denim should be rendered a vaguely casual affair. So for this dinner party, I’d suggest either light wash wide leg flared jeans (which essentially evince the spirit of a pair of trousers) with a white button up shirt┬ábuttoned up to its collar, sleeves cuffed like you’re a J. Crew pro, and a pair of dangling earrings. If it were me, I’d part my hair in the middle and then gather it back into a low pony and toy with the idea of a red lip. Maybe I’d half smudge it off before I walked out the door so my lips maintained color but not too much of it, in any prissy capacity.

If denim flare legs aren’t your thing, I might suggest a short a-line mini skirt, like this one from The Reformation with a plain white muscle tee, thick gold choker, denim jacket (but of course!) and mid-heel ballet shoes.

I put in panties in case you want to bang later.

Just kidding.

— Leandra Medine

Image via Vogue, shot by Cass Bird

  • Thamsa

    I like the first outfit idea, but I’ve been told my head looks kind of square with a middle-part, so I’d probably skip that…lol

  • Sofia Allyn

    Leandra! These are some of my favorite posts you do. Would you considering writing one on what to wear to a wedding in order to be both appropriate and festive? I’m trying to look fairly conservative in front of my boyfriend’s family (who are tragically waspy), without looking terribly boring. Ideas?!

  • Bronte

    Hi Leandra, could you possibly do a what to wear clubbing (if you havent done one in the past) in order to look cool, and not to skin showy. I always end up wearing some tight mini skirt, or crop, and feel so uncool and sheep like.

  • eclipse90

    how about this great invention called clothing? :-

  • Love the outfit ideas, but so happy I am done with dating!

  • Mr. Weston

    You can never go wrong with overalls, crop tops, and face paint. Bathe in male dingo pheromones. Put on a little lip gloss. Bam! You’re done and on your way.

  • Victoria

    thank you for carefully considering need to bang later and the perfect underwear, very thoughtful. can you write a post about what to wear for a night out to a club that you’re definitely not cool enough for, but you decide to go anyway?

  • ericarr6

    I like where my head goes first. The link for the panties is not uploading for me, can you please provide info. Thx in advance!