How to Fake Cool

If I can do it, so can you


Yeah, yeah.

Sure, sure.

There was a time, not so long ago, when I argued that you can’t fake cool. And I meant it. Part of me still believes that it is true, but then this other fracture of me says that people change! Ideas change! And with changing ideas come changing energy and when that energy turns into matter, well, we are capable of achieving whatever we set out to accomplish. Right? So recently, I’ve decided to change the narrative: if you want to look cool, then look cool. You can fake whatever you want to fake until, that is, you explicitly make it. (I didn’t write the cliché — I’m just broadcasting it.)

So here we are. Me on this side of the computer screen, you on that side, faking cool as though it is Forever 21-branded leather. But see, here’s the thing that maybe I’m leaving out — in my previous rant (or monograph, if you will), I differentiated cool from effortless, forgetting something of rather significant value about one particular nuance that makes fashion worth participating in: we get to be whoever we want to be without committing long term. By the rules of that notion, fake and effortless, or nerdy and chic, or gothic or girly or whatever all boil down to the same thing.

And that thing, of course, is you.

So maybe this is just another long winded way to say, you do you (without perpetuating narcissism) but in the spirit of “news you can use,” here are also five items that will facilitate your cool a little more seamlessly.

But enough talking, get shopping (or, you know, just looking at the stuff already in your wardrobe with a fresh eye). Here are five things to facilitate your faking cool.

1. A leather jacket, because, duh, Danny Zuko built out that account single-handedly in 1978 when Grease came out. A good version (my favorite is VEDA) is also an easy way not to compromise your summery dresses and girly shit and pridefully nerdy demeanor. It’s like the outfit equivalent of a Michelin star in that once you get one — just one — your life is basically changed.

2. Sunglasses. But not just any sunglasses and not just to be worn indoors. Because fashion is such that trends come in and go out and our perceptions of what looks good is so fickle, right now these sunglasses are round. They might retain a reflective lens though they don’t always. Sometimes they’re two tone. They are not to be confused with the round, wire frames of Coachella fame. Those convey a very different point.

3. A pair of high rise vintage Levi’s. There’s just something about the wash. They’re honest. And you can find them at most vintage shops for under $10. Here’s a guide to make that easier if you’re still not tuned in.

4. Black boots. I am not the best at black boots (unless they come with painted daisies on them) but that is also because I am not the best at being cool. Somehow, this shoe style, in its bleak lack of color, exudes an exclusive energy that makes you want to enroll.

5. A striped t-shirt. Forever the emblem of Serge and Jane — fine, Napoleon’s sailors — there is something so profoundly and inherently French about the shirt that reads, you know, “effortless.” And you know what’s cool? Being effortless. See that cool full circle we just manufactured?


There were lots of stripes in our last episode of Office Apropos. For women who have cool nailed down, check out the differing wardrobes of Maryam Nassir Zadeh, Jane Bishop, and Meredith Kahn. Katie Sturino proves cool isn’t about size, and this kid proves it isn’t about age. Being in a band definitely helps, though. Good news: you’re already in ours.

Get more Shopping ?
  • Vicki D.

    if ya can’t drop $1200+ on veda…all saints makes a similar one for less than half the price.

    • Giedre


  • Eleanor

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  • Elizabeth Tamkin

    Your style is very French. Are you Jane Birkin?

  • I’ve got on my high-waisted, light blue Levis right now. Surefire way to feel a little more at ease. Caught my reflection in the subway door window today (I know, what a narcissist), and I was like: you know what, not half bad, even kinda cool.

    Thanks, denim!!!!!

    • Leandra Medine

      And a much cooler-than-striped top. SHOW THEM SHOW THEM

    • tonikali

      But like, how do i deal with the camel toe/crotch bunch ?

  • Catalina
    • this really makes me wish i was alive in every decade…except 2005…the horror.

    • Bella Charlwood


  • I totally believe in faking cool. Walking alone into school cafeterias (the ultimate judgement zone) used to be so terrifying to me until I did this trick where I say to myself, “I’m the shit!” until I really believed it. Funnily enough, this trick of “faking cool” helped me through a lot of social situations.

    • Stephanie

      Agree! Confidence goes a looooong way!

  • Kelly O

    Step 1: Dress like a Ramone
    Step 2: Done

    • Aydan


    • Amelia Diamond


  • cool boyss..

  • Annie Anzaldua

    Faking feeling cool is totally an awesome trick. When I start to feel awkward I just pretend that I am awesomer than I really am and then BOOM…insta-cool vibe.

    Love this post!

    Annie Abbey //

  • parkzark

    Cool kit!!

  • KrisP

    I would add to this any one of the multiple wraps from Aritzia. I have a few – you can wear them with a blouse, the leather, all of it! Seriously. Effortless and cool!

    • These are my holy grail item. Comfy, warm, and they go with EVERYTHING.

      • Kris Peterson

        For reals. I have about 6 of them now. They are a must have, all-season item here in Seattle!

  • Lyric

    This is the outfit of pretty much every guy I’ve ever had a crush on. Minus the boots, but adding converse.

  • Claudia Tetreault-Percy

    What a great read! Now I know what i’m wearing tomorrow to be super kewl. Thanks Leandra.

  • Leandra did you watch Grease last night TOO?!

    • Leandra Medine

      I MAY HAVE

  • Catalina

    or be like Kyemah McEntyre and forgo all rules

  • CaturM

    White sneakers.. They give you that effortless cool look and are basically a chameleon when you can’t figure out what shoes to wear

    • Amelia Diamond


      • I knew you would appreciate a good dance number <3

  • ashleymaciejewski

    For sunnies, I’d start here:

    • Esther Levy


    • Amelia Diamond

      ugh. way cooler than me. SHOES?

      • Zara!
        Where all the fake cool girls shop =)

    • Leandra Medine

      YOU WIN

    • Dawn


  • Tiana

    Funnily enough most of this will have be worn by my mother back in the day – yet is still cool

  • Greer

    bassike for the striped shirt!!! not fake cool legit cool my god so so cool

  • Candy Rose

    I like the striped T-shirt!

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  • It’s so true Leandra. Make it until you fake it, but regarding being cool there are ways to be cool without being cool, if you know what I mean. The core of it is so damn owing a damn leather jacket and some vintage levi’s, because there’s nothing better than this. It’s exaclty the definition of my style, and as a French blogger, I feel like we’re connected.. Haha x

  • Hadley
  • cocoO

    Leandra I am going to paris next week and want to get an awesome leather jacket what are your recommendations in places to shop? or should I just buy it on line?

    • Leandra Medine

      Get a Veda one! The Jayne!

  • Person Yay

    why don’t you guys ver take into account the prices of these things?

  • Isabela

    can I fake cool with brown boots and wayfarers? please tell me I can!

    • Leandra Medine



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  • Divya Keerthika

    “makes fashion worth participating in: we get to be whoever we want to be without committing long term” (y) That is what I love most about fashion – that it’s change is constant.

  • Linda S.

    I read this I though that wait, I have these things- lets try to put them together!

  • H

    My round sunnies and black boots scare boys. Im winning the cool game

  • Not Constantinople

    The most important accessory = insouciance.

  • Juliette Kuiper

    I’m searching for this jacket for a month now – can’t get it out of my head. Can anyone tell me where its from or where I can buy a similar one??

    • Leandra Medine

      hi! that jacket is rosie assoulin