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.

Date Night Outfits Style Leandra Medine Man Repeller-53

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.

Date Night Outfits Style Leandra Medine Man Repeller-27

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…

Date Night Outfits Style Leandra Medine Man Repeller-2

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.

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  • Mariana

    My heart beats louder for that Saint Laurent blazer with perfect length.

  • Savannah

    THOSE MR shoes though!!!! Just how soon are they coming?
    Need to budget for them.

    • Leandra Medine

      End of Feb!

      • Pandora Sykes


  • Federica76

    Today is International Day of Zero Tolerance for Female Genital Mutilation. http://www.un.org/en/events/femalegenitalmutilationday/ The fact that none of us feminists, Muslim women or Hollywood stars spent a word, let alone organised a march, to speak against this crime is a real shame.

  • tmm16

    The Calvin Klein slip and Saint Laurent blazer.. might want to get married in that look. Amazing.

    • Natty

      Seriously. It’s making my heart flutter.

    • Leandra Medine

      You can borrow from me. Would be my froggin honorn

      • tmm16

        Dreams do come true. I may certainly hold you to it! @LeandraMedine:disqus

  • onimaki

    So in love with the second look!! Now I want to quit on guys entirely and just date that trousers+sweater set <3

  • Cara

    Since those amazing Topaz earrings are sold out, any chance the MR team has ideas on where else one can find some big ass earrings? Also maybe ones that cost less than $300?

    • Leandra Medine

      Etsy! I will fine for you

      • Cara

        You are amazing, Leandra!

  • Love it all! Best dating advice ever.

  • Irene Roberts

    Leandra you look gorgeous in look #1!!!!! Sexy and simple, I love it!!!
    Also, I NEED your new shoes in look #3!!!! When are they coming out? LOVE them!! And thanks for the Carrie reference, I love that line. So kick ass!

    • Leandra Medine

      Hey!! Coming out end of Feb 🙂

  • Daeyz

    love the looks, so great!


  • Natali

    I would most possibly wear the first combo but the 3rd one is my most favourite look!


  • Caro A

    One time someone told that it’s a fact that you’re your best self on a first date. And I questioned her and she was like, “no, it’s true, it really is”. And I still think about it five years later, and I’m mad about it because that is the OPPOSITE of a fact. She also told me not to worry about meeting a guy because he would come along. She said it was a huge waste of energy and now that I have a ~guy~ I still don’t agree with her because I’m pretty sure all that anxiety and anguish I had got me to a good spot. Wow. I digress. Sorry. Maybe I shouldn’t take advice from this girl anymore. Wow, those G.D. Dries pants make me weak.

  • claire

    that calvin klein slip dress is everything! love, love, love the entire ensemble.

  • Rheanonn Clarissa Perez

    ooh wear the month 6/month 3 outfit on the 1st date to see if they can really get down with ya 😉 lol


  • Lanatria Brackett Ellis


  • chouette

    Holy shit if you showed up for a dinner date with me in that I’d be so intimidated I’d probably leave for the bathroom and never come back. TRES PROFESH.

  • oliviafortune

    Bought to climb every mountain for that the Row polo 💔

  • Anne


  • Marina Camu

    Look #1 reminds me with black tight and YSL blazer reminds me Vogue Paris vibes in 80’s. So glamorous and sexy!

  • Juliana Salazar

    new MR shoes are so gewd!!!!

  • im loving those MR by MR sandals.
    congrats on the line

  • Kaylyn

    Adoring the third look, so fun!

  • Sindy Tshuma

    Been hunting those Celine shoes in the 1st pic for ages now. If anyone knows where I can get the same style (even by another label) by all means let me know 🙏🏾.
    Leandra – on point as always. Bravo on the outfits lady, 👏🏽👏🏽👏🏽👏🏽. Keep reppin’ all us Man Repelling chicks. I live vicariously through your wardrobe. 😻😍❤️💃🏾👍🏾👏🏽

  • T_uhwerp

    I’m in love with the green clutch affiliated with look #2! Who is it by?

  • Shulie

    Leandra, you are so beautiful!
    Happy Everything!

  • Merrynell

    Look #3 though! From barroom to bedroom.