3 Outfit Ideas for a Date


It’s been a long time since I ran this rodeo, but I have an opinion or two about what I would wear in the event I were still on the ~dating circuit.~ (It is different from these sorry-ass recommendations, but I still stand behind these.) But more interesting than cogitating on outfit ideas for first dates is the prospect of identifying the progression of a relationship vis-a-vis what you wear. How would I conduct myself over the progression of dates with a single individual spanning six months?

If you’re confused, don’t worry. I’m about to demonstrate.

Month 1: You just met, this person seems great, date #1 is at a fancy restaurant.

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Saint Laurent blazer, Calvin Klein dress, Falke tights, Céline shoes

To be honest, the actual outfit doesn’t matter. The goal is to wear something that makes you feel like a good version yourself. Note it doesn’t have to be the best version of yourself — that is an annoying and somewhat impossible standard. So the thing with this outfit is that whenever I’m feeling like shit, I put it on, think I look great and boom: problem solved. Also worth noting is that it’s kind of ~sexy~ in that way slip dresses and sheer tights are. And yet I still feel like myself. Nutritious!

Moving on.

Month 3: It’s been going pretty well, you seem to like each other, you might even go so far as to say you’re dating. You’re going back to that fancy restaurant because apparently, this person you enjoy so much is not creative when it comes to event planning.

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Dries Van Noten pants and sweater — another option here, The Row polo — similar here, Alessandra Rich earrings, Aurélie Bidermann bracelets

LET IT OUT! LET IT OUT! He (or she!) should know that when you’re emotionally recovered from feeling like shit around the time of date #1, it’s all leopard print and varsity V-necks punctuated by polos. The earrings are your flair. But it’s your heart and soul that contains the best and biggest secrets.

Month 6: You’re in the ~comfort zone~, what a fun place to reside. Comfort can mean a number of different things for different people. For me, it’s unapologetic allegiance to the style cues of one Carrie Bradshaw and…

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Willa & Mae robe and pants, Staud top, MR by Man Repeller sandals, Rejina Pyo sunglasses

Loungewear as outerwear. Will we get into a fight that will catapult me across the street in true Carrie fashion so that I can run and run and run and yell something like, “You can come ’round this block all you want, because I DON’T LIVE HERE ANYMORE”?

Here’s hoping.

Uh, I have to go, bye!

Photos by Krista Anna Lewis.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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