Going on a Date? Wear This.

Leandra Medine | February 12, 2016

Don’t forget your Chapstick.

I know what you’re thinking — in some ways, I’m thinking it, too: Who am I to give you dating advice, right? I’ve built a business on the art of repelling men using expensive footwear and sometimes pants that flare just a little too wide. And this, this in spite of the fact that I was married at a tender 23. So, really, am I the authority on what you should wear if you have a date slated for this week?

But I ask you to consider this: Amelia, who typically likes to scribe these stories, is still single.

I, on the other hand, am not.

So, let’s proceed! Shall we? The way I see it, if you are, in fact, going on a date, the three most likely scenarios under which you are to find yourself are as follows:

+Day date

+Evening drinks

+Some version of an event where you will be among his or your own friends to make it seem more casual

So what’s a girl to wear?

For a day date:

Fendi fur coat, Acne denim jacket, Miu Miu cardigan, We11 Done pants (similar here), Converse sneakers Fendi fur coat, Acne denim jacket, Miu Miu cardigan, We11 Done pants (similar here), Converse sneakers

Converse will trick your opponent into thinking that you’re cool. Interesting pants that are casual enough not to raise eyebrows but still dynamic enough to raise like a single follicle in one eyebrow will suggest there is more to you than meets the eye. More than your fupa, even. Black pants look cool when paired with a denim jacket. Denim jackets look great with black coats over them. I’d recommend something red under the panoply of non-color because you, my friend, are the life of the easel.

For evening drinks:

Date-Outfits-Leandra-Medine-Man-Repeller---13 Atea Oceanie shirt, Re/Done jeans (another option here), Miu Miu shoes, Topshop socks

I ask you to consider what you would wear if you were having drinks with a close friend who you haven’t seen in a long time, who you’d also like to make a good impression on because it’s been so long and last you heard, she’s got a great job and maybe she doesn’t realize that you have a great job, too, that you’ve totally moved past Limited Too and practically have Phoebe Philo on speed dial, though you still appreciate a pair of conversation starter shoes, so! Lo and behold: your most reliable pair of jeans (are they high waist? Are they flared? Maybe they should be?), with a striped, long sleeve t-shirt and a button down of your choosing layered over the t-shirt. If you want to add another layer to the onion, I ask you to consider socks that strike in another direction.

And as for the shoes? Show stoppers, please!

For a vaguely dressy party wherein multiple members are involved:

Date-Outfits-Leandra-Medine-Man-Repeller---7 Topshop jacket, Gucci tank, J.Crew turtleneck, We11 Done skirt, Céline shoes, Wolford tights

You don’t necessarily have to look like you’re about to cry, but I’d ask that you pair two of your favorite garments of the moment from the pile of Shit that is Outlandish in your closet, break them up with a simple knit (a tissue turtleneck rarely fails) and then try flat shoes because wearing flats on a date makes running away much easier.

Of course, if you don’t have a date, just text me. I’ll be eating goat milk ice cream in bed and watching terrible, terrible TV.

Photographed by Krista Anna Lewis.

hyperlink-gif-20-date-outfits

  • Yates

    These are my favorite articles on the site! No one styles like you, Leandra, and it’s perennially inspiring! Also brilliant idea to quickly weed out potential suitors who recoil at flared crops.*

    *I count three plant-related words in my comment. I think that’s something.

  • Sarah McCarron

    Wow. That mink jacket over denim: GENIUS.

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  • Alessandra

    The Miu Miu shoessss you got on sale <3

  • Whisjoga

    Yes Leandra!!!!!!!!

  • those Miu Miu, I’m in love..

    xx
    http://www.cherry-mag.com

  • Andrea Raymer

    I’m with you on the watching terrible TV thing, The Bachelor Valentines Day special is on, and I couldn’t possibly miss it.

  • anoni81b4u

    I enjoy women who wear conservative clothing appropriate for their culture.

  • Patrick Altorre

    I’ll been looking for this kind of information, and good thing i have found your blog thanks for sharing I enjoy reading it so much, her is my fashion blog for Ballet Flats please visit http://www.fzillion.com

  • BK

    Love the looks – except for that Fendi jacket. Rabbit is not an ethical fur!

  • Stephanie

    Nice pants and jeans <3

    http://www.stepfromsteph.blogspot.com

  • Forget about it! Who needs a date when you can wear wide jeans and stripy socks while watching Netflix!

    Claire
    http://www.theclassycatalogue.com