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So, You’re Going on a Date, Right?

What do you wear?


In collaboration with H&M Life. 

Look, I’m no dating coach.

I spent the three years that my now-husband and I were broken up calling him on an unrelenting weekly basis to check whether his temperature on the thermometer of love-for-Leandra had changed in my favor. Through the course of the three years, it never ever changed UNTIL ONE DAY! when he saw me exiting his building on Mercer Street with an English man, who I was about to embark on a first date with.

I was wearing a shin-length skirt with a white button down blouse, which I had taken from my youngest brother’s closet, and a pair of devastatingly basic Chloé gladiator wedges, which I had not taken from my youngest brother’s closet even though I wish I had.

I went over to say hello because I am a gentlewoman and he reciprocated the pleasantry. Then he text messaged me to say that the encounter had “physically hurt,” to which I lent absolutely no credit to handsome English man who stood to my left during the encounter and surmised that CUHLEARLY, my outfit has incited his heart’s starting to sing an *NSYNC song that made him (guitar solo please:) want me back.

Now that I am married de facto, I don’t think it’s in your worst interest to take my dating advice. Especially, I might add when it is deeply imbued with the sartorial pursuits of a first date outfit. Because, think about it. When you’re about to enter a first date, you don’t really know who you’re meeting and he (or she!) doesn’t quite know you either. Without using your mouth, it seems like your prerogative should be to convey a point about who you are.

And how do you do that?

With clothes.

If you fancy yourself a man repeller, the first date seems like high time to experiment with two of the most boring silhouettes a woman can engage with: the button up shirt and the pencil skirt. Why? Because nothing says I am a ball of ecstasy (the non-narcotic kind!) like making said boring silhouettes look like Fun with a capital-F.

Enter the photographed, embellished skirt from H&M and the corresponding striped shirt by Steven Alan (or this funky sleeved one from Topshop).

Because it’s 2014 and currently de rigeur, I’d also suggest a pair of mules, sparkle heel notwithstanding but again: think about upping the fun factor. Take a handbag (in case he sucks and you need somewhere to throw up) and a pair of reflective lensed sunglasses because even though it might be night, for the sake of thematic consistency (speaking without your mouth), in the event you do like him, you might want to put them on to demonstrate how bright his future is.

Worst comes to it, the date sucks but the way I see it, you still win. Hard. Why? Because your outfit ruleszzzzzzzzs.

Part of a collaboration with H&M Life. 

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  • Desiree Hill

    Question MR, what would your ideal spice-it-up/ i’m not your boring wife 5 years before we even get married, date night outfit for a preexisting relationship be? He dresses down and quite..unfashionable, so rocking my snazziest heels would make me feel uber awkward. Sneakers and boots make me feel too basic, and jeans are redundant, especially when I wake up the next morning to throw them on for our routine trip to PetSmart. Helpppp!!!


    – Desperate.

    • Never doubt the power of a seriously red lipstick.

      • Kiwi

        Colleen-or the hottest pink? pssssssst–its Kaley! Lets wear crazy lipstick tonight! xoxo.

        • Psssssst I did like your lipstick! I didn’t get the memo in time.

    • Leandra Medine

      Desperado!!!!!!!!! sneakers and boots don’t HAVE to make you feel basic if you wear them with a. mini dresses that are also ball gown apropos, b. nakkid, c. short skirts, preferably chiffon or tweed, d, leather pants (for sneakers), e. nakkid

    • I say go for it. Maxi dressed slashed to the navel and arse crack front and back, with black as your soul lipstick. Maybe shave your head. You would look fierce.

      (I may be joking but are skinny jeans and heels an option? Or something dressier with an oh so casual jacket to dress em down? Failing that SLASH IT TO YO BELLY GIRL)

    • Abby

      I know I’m definitely not MR but I read your question and thought of some solutions of my own. For one, do you own a nice pair of straight legged trousers? (not talking about the stretchy kind people often wear to work, I mean a nice, tailored pair maybe of a navy color) They are always great because they can be easily dressed up/down. I would pair the trousers (a step up from jeans, but not quite as dressy as a skirt/dress may be!) with a great pair of flats, and then a button up shirt. Or really whatever shirt suits your taste! Whether that be a cardigan look, or even chambray. Anyways, just make it your own!

  • Thanks for advice! Very cool outfit!

  • kittendelight

    That outfit is horrific! Delicate lace with a stripey business shirt? What?

    • Desiree Hill

      Whaaat? Your hatin. That outfit is awesome and well put together! The yellow lace skirt juxtaposed to the wide vertical striped classic blue and white shirt presents the perfect color combination for the seemingly delayed arrival of spring. Along with that, its says “I’m not a little dainty fairy, a mere figment of your preconceived imagination that I am all beauty and no brains”. It shows versatility, maturity, and most of all creativity to go above the conventional “date outfit”.

      • kittendelight

        Yeah I really don’t like it but it’s not a personal attack on a person, I just think it clashes horribly and doesn’t work. I can appreciate outfits that I wouldn’t wear on other people but I just don’t think it works at all. It’s nice that you can see it in a totally different way and appreciate it though 🙂

  • GapToothedGirl

    I’m not into lace…I don’t know yet if I like it or not… Mumble…
    Love, Gap.

  • coffeetoo

    yes, yes, and yes!

  • Irene Laura
  • Rebecca

    Oooooft, when I look back on my last-first date I’m not sure why I wore that. It wasn’t too dressy but maybe a bit too cool, oh well.

    I’m happy that your happily married but TUT TUT for your man taking 3 years to change his mind

  • I love your heels and your clutch Leandra, you look fabulous!!!

    Mafalda ❤

  • liz

    I actually had a conversation last night with some friends about when persistence goes from being a creepy nuisance to incredibly charming and sweet. Sometimes it takes a minute (or three years) for someone to really get you. I love this, all of this.

  • monkeyshines
  • Elizabeth

    So, wait a minute – I’M THE ONLY ONE THAT THINKS THIS OUTFIT IS TOTALLY INAPPROPRIATE? I realise that this is Manrepeller and no one loves this site more than I do, but this outfit would scare the BEJEEZUS out of any man! Leandra’s husband is obviously not the norm, he’s MARRIED TO THE QUEEN MANREPELLER! Any other guy you’re meeting for coffee or whatever would be terrified as soon as he sees that shirt.

  • I kind of hate the return of the mule trend, but I’d come around for these babies. Love your classic taste with a fun details twist.

  • I’ve been eyeing this lace skirt…well something like it. So I saw this, this morning…and then the skirt went on sale today. Purchased! Now I have to find some cute shirt for it.

  • Sarah Nesbitt Artecona

    Is it MR-ish not to get a pedicure?

  • As a purveyor of some sort of rear-end curveage, I’m a huge fan of all of these skirts. Definitely taking cues from this post. Cheers!

  • Kate Wilson
  • Pink angel

    Been looking for a clutch like the for years…any tips? Not looking for the high end version.

  • maud.schellekens

    Cool look, love your mules!

    XOXO Maud


  • Vika Arinicheva

    I miss the lessons in layering 🙁

  • Victoria

    That outfit is a definite man repeller! hideous!

  • BoyfriendsandBlazers

    lurrrveee it. I was living in Great Neck with my ex when I came out wearing a pencil skirt and a button down top. His first response is you look like you should meet my parents for the first time. Most girls would be thrown off and not excited about this comment, but I took it as the most flattering complement. He was saying you look mature, eloquent and sophisticated. If you understand @leandramedine:disqus ‘s look you understand it’s about sophistication and personality.

    • BoyfriendsandBlazers

      maybe?! @leandramedine:disqus

  • lizzie

    Looks great!
    Also adding a cashmere piece brings an outfit to life!

  • JimmyFooIsMyBitch

    This is so cute. You are so cute. I love how you write for your readers who want to know you, but also want your expertise. 😉 Keep it up lady

  • Margo

    It doesn’t matter what you wear. The guy just wants to get laid. That’s it in a nutshell. You could wear a potato sack and it wouldn’t make ANY deference. Wear what makes YOU feel good. Just remember that and you’ll save a whole lot of time wondering what to wear. Men don’t give 2 shits about what you wear. WOMEN DO.

  • April Serio

    lol…I love the way you write

  • I love this outfit SO MUCH idk what everyone is hating on. Mules, collar, clashing shirt & skirt — literally perfection. In an attempt to copy I even bought the skirt recommended in the slideshow at the bottom, and last month, spent an insane $340 on THE PERFECT COLLAR after seeing it on Leandra.


  • great skirt!! is just super femenine!!