Cool vs. Effortless

It’s Personal Style day on Man Repeller — feast your eyes on this.


I have always wanted to look cool. To be the kind of girl who not just makes you think you can do that too but forces you to want to try it. I want to exude that sense of: she could be wearing a potato sack and still look great. Maybe in fact, in that last approximation, I am wearing a potato sack.

Fundamentally, though, I understand that I’m not cool.

You can’t fake cool — cool is inherent and you either are it or you’re not. This means nothing about style other than, I suppose, that to be cool immediately vaccinates a woman (or man) against bad style. Think Johnny Depp or Daria Werbowy or Erin Wasson. With Depp’s hair so dirty it is almost dreadlocked, or Werbowy’s insouciant nose ring and dirty white tank tops, or Wasson’s ripped shorts and desert boots, these icons-in-their-own-right emit a sense of style that we love not because of the clothes but because we’re attracted to the swagger.

It is effortless by definition, though interesting to note is the fact that “effortlessness” as a style movement can be faked. And well, at that. If it’s true that good artists copy and great artists steal, then when it comes to fashion, effortless dressing is at the crux of this saying. Designers like Phoebe Philo or Clare Waight-Keller — with their clean lines and silhouettes that whisper, not yell, with great aplomb — have mandated so.

This is arguably what has incited the viral concept that is “normcore,” but something people fail to recognize quite frequently with normcore is that looking like you didn’t try — pairing flip flops with jeans and a silk blouse, or a dress with dirty tennis shoes — doesn’t necessarily mean you’re in style. You might be on trend, but when considering the umbrella of style, which does not shield the pour of trendiness, there is another variable at play and that is impressiveness.

I have deduced, based on conversations with friends about the garments they say they’ll never tire of wearing, and images of Anna Wintour, standing relentlessly and with poise in her Manolo Blahnik sandal mules, that good style doesn’t aim to impress anyone but the self.

It’s a private conversation between the wearer and the clothes. Wintour, along with any of the aforementioned friends, choose the items that they choose to wear over and over again, not taking into account a third party opinion that might role its eyes at the redundancy, because the items, whatever they are, suit the wearers.

They make them feel like the realistically best or most accurate versions of themselves.

These “versions” may appear polished because that might be someone’s sense of effortless. They might also not, but at the respective core here is either the illusion of effortlessness or an accurate portrayal of it. And no matter how you slice that, a new progeny is born and that is authenticity.

Now to be able to fake that seems pretty damn cool.

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  • Britta Newton

    Leandra- you are cool. Your personal style is intrisic to thinking outside of the box, and trying new things but the way you pull it off seems effortless, IE cool. You have the swagger and curiosity of a young girl playing dress up in high fashion clothing! Anyways, great post.

    • I agree! You are way cooler than you think – and plenty of people want to do what you do…no matter how crazy you think that sounds!

    • Amanda GREY

      Leandra seems to me to have BOTH. Cool but also classically nonchalant or “effortless”. That balance is what creates her style gravitas.

  • Love the ease of “effortless” style. It’s such a modern-classic way of dressing.

  • Cassandra Vallée


    I’m such a freakin’ quirk that sometimes the line between being passionate about fashion and trying too hard is blurry.

    And that’s not cool.
    ps: leandra, you’re at the highest on my cool-o-meter. And Erin rocks.

  • I think part of being cool is being unaware of your coolness. If you’re aware, it become conscious and effortful, which immediately puts you in the fake category. You may be a total dork (in the best way possible), but you definitely encourage me to take risks and have fun with fashion. And that’s pretty damn cool.

  • IsisdePaname

    I love jane B !!

  • Love this…cool and effortless are always in…however true effortless style isn’t ever trying to be cool, just is 🙂

  • Eduardo Rolo

    this is why I read MR! I if wasn’t gay, I would love you to be my “style” crush, but since I am… I allowed you to be my spirit animal! Sound like a deal. Love you, Leandra

  • Cyn

    Hol’ up! I think you’re cool, and feel cool for thinking that, does that mean we are both not cool? AWKWARD.

  • I like the text, but according to the pictures being cool or/& effortless is actually just being tall and thin. A plumpier version of E.A. in simple shirt and pants like in the pic would be a random lady rather conservative. Here in Argentina we have plenty of that.
    Even though I’m tall and thin I think I detest this visual approximation.

    • Alya

      I was 100% just going to comment the gist of what you just wrote. I think any style of cool should include women who totally own body types that differ from this (unfortunately) ‘textbook’ standard of cool. If cool’s about swagger, then size zeros are not the only one who possess it.

  • Murjani

    It appears your vision or interpretation of cool entails copious amounts of denim, and a deep wish it were 1993 again. You, my dear, rise way far above that. No fear, your effortless cool is in a class all its own.

  • Amelie Sebastien

    I agree with Mika M below, what looks cool or effortless on a tiny or lanky gal looks decidedly different on someone with a little more meat. Loose things don’t drape as nicely and the whole “sheer white T” concept is no longer as appealing when you need a bra with some serious support as opposed to pretty lacy triangles. Plus, those of us with more curves (I hate that word, but haven’t yet found a suitable alternative) generally like garmets with more structure.
    What looks effortless on someone larger than size 4?

    • Leandra Medine

      So I feel like the point I obviously did not articulate clearly enough is that effortless varies person to person. One woman’s polished could be her effortless while another’s nod to the victorian era could be hers. This obviously also varies according to size and the reason the photos represented look the way they do is chiefly because I am constantly in pursuit of that vaguely unattractive little boy look

      • Kate

        vaguely unhealthy little boy look

      • Effortless Everyday Style

        Leandra you Effortlessly, in your own style are a Style Icon just as Erin Wasson. When you wear what you love and are true to yourself and not trying to look like everyone else, then you have achieved Effortlessness

    • Danaë Botha

      Yeah, there were no examples here, but they exist obviously. Rita Ora and Rihanna (while not exactly plus size) are definitely curvy and have their own effortless (and quite sexy) style that doesn’t rely on gamine shirts. Rihanna especially likes to create space around her body and at a towering 5’9”, that’s a bold choice (as a tall, curvy girl myself, any time I try introduce “space” I end up looking like the purple teletubby)…

  • Ana Lu Garro

    I agree with this completely! But I don’t really think the people we label as cool really think that they’re cool. I’m pretty sure they feel the same insecurity when dressing up and then say well fuck it I’m going out like this anyway.

    Ana Lu from Things&Crowns

  • Arielle McManus

    can we PLEASE stop using the word effortless. that’s a word that has to die. it is used to describe things that, 99.99999% of the time are not, in fact, effortless, and actually take A LOT of effort.

    • Leandra Medine

      but when it’s used appropriately, it’s *so* accurate

    • Amanda GREY

      Hate for words is RIDICULOUS. Don’t use it, but word have meaning beyong one’s prefference.

  • Léa

    I feel like this has a lot to do with attitude as well. You have to truly beget an air of insouciance. I can dress up in a hip outfit for a night out but I’ll probably look like I’ve put a lot of thought into it. Style has to be effortless, otherwise it’s not really style.

  • Effortlessness can be cool but cool can’t effortlessness. Let’s be honest not this really effortless in fashion even your dad jshorts was purchased with specific intention (whatever ill-vised they may be.)

    I do agree with you “on trend/in style” theory. I will add, its all about personal style; how can one wear whatever else is donning but look totally different in. Is effortlessness cool to me.

  • mjlifestylist

    I used to have the same overwhelming desire to join the “Cool Girls Club” – until I turned 35. I’m not exactly sure what made the shift happen, but suddenly I just did not care. There is a freedom that comes with age and I wish all you girls in your 20s and 30s could see your future selves to breathe that sigh of relief knowing that you ARE the Cool Girl when you just don’t care how many likes you receive on your instagram post.

  • A person style become effortless and cool when is an extension of his/her personality. If I wear what I love and not what others like, then I’m effortless.

    TROPICAL PRINTS…new post at:

  • Kristen

    Whenever I dress simple, or try to look “effortless,” I never know if I look too…boring. But that’s just me, all the photos were really inspiring

  • You’re not cool. You’re the next level of cool.

  • Intan

    Amy Winehouse was effortlessly cool, it’s because she wasn’t aware of her coolness. But yeah, she was. You can dress up like her, be it beehive hairdo, heavy winged eyeliner, with tshirt and dirty jeans (and even dirtier ballerina pumps). But if you don’t have that “cool aura”, you’ll end up in that “fake cool” category.

    And Leandra, come on! You’re effing cool.

  • Lexie Miles

    maybe soon (er rather than later) the new cool will be the un cool?

  • Andres Poiche
  • Elisa Taviti
  • zoe_whip

    I think cool it not giving a shit what other people think. It’s just being you and being okay in your own skin. Confidence is inherent cool.

  • ee_by_cc

    Completely agree that all “cool” looking style comes from an innate sense of self and comfort with self. It’s more of an energy that emanates from that person rather than the actual clothes they’re wearing. Spot on, as usual!

  • When you search photos for the slideshow, where do you search? Because you always find so many good ones!

    • Leandra Medine

      That is a question for charlotte THE VISIONARY

  • monique

    Much of it is “styled” so I can’t give credit to the wearer. And yeah, they’re all pretty cool but it appears to come with also being beautiful, thin and somewhat (or a lot) famous. I’m more impressed with people outside of the entertainment or fashion industry who have great style. Being cool is in the eye of the beholder. Models cool? What a concept.

  • Tina

    Roll not role!
    Loved this piece x

    • Leandra Medine

      Typos always win/proof reading never does. Thanks

      • Lindsay

        You might also want to rethink this part: “With Depp’s hair so dirty it is almost dreadlocked”

  • Amanda GREY

    Cool Vs Effortless, kindda two sides of the same coin: one side more edgy, and the other one more conservative, but definitely complement each other. Cool, if burdersome and contrived is off-putting, BUT effortless without a wink is not that memorable. I preffer both! That “art” is what makes style truly authentic!

  • ienard118

    I have several summery graduation parties these coming weeks; what should I wear to make me look “cool” without looking prepped out for summer or that I tried to hard?

  • Tess Harrison

    I think it is curious / awesome all the photos you chose to illustrate cool style feature women in comfortable, flattering and modest clothing. No one’s tits are out. No one has uncomfortable shoes on. I think cool style can synonymous with comfort and ease. There is a cool power/badass-je-ne-sais-quoi that goes hand in hand with modesty.
    And stop it. You are the coolest chick.

  • Jesús Sire

    No, she’s right. Leandra is not cool. She’s tries very hard, just like me. She’s creative and trendy, but she doesn’t have that intrinsic coolness. Is what French called “nonchalance” and it’s different from normcores trying to forget their hipster past. Is Emannuelle Alt and Grace Coddington. Depp and Moss also.
    (Anyway, this is a cool article, L)

  • Catherine

    I feel like being cool is not only dressing for yourself, but being confident. I think body image issues and not being super skinny creates barriers to just wearing things because you like it. I walked out of the house this morning feeling great, but later I just felt big and overdone and not as hip and 70s as I did in the morning.
    Cool is about confidence. Not just garments you love but loving yourself.

  • erin

    You don’t have to be cool for others to like you.. Be yourself is the best way to have others acknowledge you and if they don’t think your cool enough then you don’t need them to be a friend. The beauty of fashion is in each others eyes what you liked and enjoy wearing.. Don’t change for anyone unless it is for a positive change.. You have to be happy and cool with your self.

  • trixahdeshade

    Isn’t the word that defines this the Italian one- ‘sprezzatura”?

  • mgbbilly

    Your site sucks. I clicked on an image because I wanted to see the image. Imagine that. Did I get to the image? NO

  • Marta Millere

    Absolutely adore your blog, Leandra, and I too have been in the pursuit of ‘cool’ ever since I started to care about what I had on (when I was 9 years old I think and realized that my Ninja Turtles t-shirt looked insanely cool paired with my threadbare jorts). Being ‘cool’ and ‘effortless’ goes hand in hand and with that in mind, you are très très cool, because you don’t take yourself too seriously, or so it seems. Not caring too much about what you’ve got on + making your own style rules + being confident in your own skin = recipe for coolness in my eyes. Baci from Rome

  • kyzmeto

    Cool = cheekbones and thinness.Nothing more, all the people mentioned are only cool because of their genetic inheritance. If they were not blessed in the lottery of looks you would just be thinking they were an odd man with dirty hair, and a girl whose washing machine is broken.

  • I guess its your love for 3 inch clogs and sandals that might sometimes bring down the effortlessness in your look. But you’re definitely the coolest person when it comes down to style , fashion and even everything else.

  • effortlesseverydaystyle

    Loved this!

  • Amazing post.

  • Victoria

    pictures #12 and #13 are complete opposites but i’m in love with both, so so much

  • Great post! But Leandra don’t fool yourself.. you’re cool! 😉

  • Blog de Nuria
  • Babyslice

    But wait … we say this in full awareness of Johnny depps wide array of pinstripe fedoras/vests ?!