Why I Stopped Caring About Being Cool


I have spent the greater half of my 20s trying to figure out the je ne sais quoi that defines what it means to be “cool.” I know that runs counter to what it means to have je ne sais quoi, but I also refuse to believe that I can’t figure it out. At 22, I called it swag and believed we all had it. At 24, when I learned we don’t, I demanded that you could fake it until you made it — just wear leather jackets and sunglasses and ripped blue jeans until the cows come home.

At 25, I realized that you can only fake it for so long, and thus changed my thesis. Instead of trying to become cool, I would publicly announce the difference between “cool” and “effortless” and haphazardly dub myself the latter.

Now, at 28, I wonder why I cared so much about this worshipped (but somewhat unimpressive) four-letter word. Is “cool” the best we’ve got?

Frankly, I’ve never actually self-identified as cool (no “cool” person would ever spend so much time and so many words trying to weasel their way into it). I have wanted to, I have tried to (see above) but I consistently land on a singular reality: I am not cool. Not the way I have heretofore known it, at least.

But hey, that’s okay. Because what even *is* cool? And when did we (sorry, am I projecting?) become so obsessed with identifying as cool?

For as long as I’ve carried the word around, I’ve associated it with models off-duty wearing leather jackets and smoking the kinds of cigarettes that don’t kill you (I mean, they do, but cool people are too cool to care for nonsense like that). I see soft eyelids and a relaxed jaw and a sort of nonchalance which I have never maintained. But that’s just it — I’m associating the word with a visualization that is not necessarily reflective of the de facto definition.

My best friend Google imparts the following: to be cool as an adjective is to be “fashionably attractive or impressive.” Of course, what it means to be “fashionably attractive” changes as frequently as one blinks. It’s a consistently mutable state. So how is it that for as long as I’ve chased cool, I have thought to myself that I need a leather jacket and ripped jeans? I guess I was just trying to get in character. That by wearing the clothes, I’d become the thing. BUT GUESS WHAT? I am who I am and who I am is neurotic, multiple layers, afraid to die from tobacco, a lot of bright colors. My jaw is permanently stiff. I’m a maximalist! There’s a pineapple stitched into the back of one of my coats and my eyelids are only ever soft when I’m asleep.

All the refined and simple stuff that makes someone look cool? I can’t handle it. And all the characteristics that actually make them cool are the precise reason I’m not it.

But here’s my question: How can one possibly force themselves to be laid back? That concept is at complete odds with being laid back. What I have to do, obviously, is accept that I am how I am. Appreciate that for its inconsistencies and idiosyncrasies — the good and the bad. Feel comfortable divorcing myself from the prospect of becoming anything but who I am. Maybe then I’ll hit my “flow,” as the yoga community might call it. Wouldn’t that be cool?

(Sorry, I had to.)

Photos by Krista Anna Lewis.

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  • Lanatria Brackett Ellis

    At 28, I also feel the same way.To me, cool is just having an ‘ is what it is’ attitude. Cool is more like a state of being.I would never say I am cool because cool kids don’t say that but,yea…(I fancy myself a cool lady).

  • Every time I want to be cool I start snapping my fingers and get into formation for the next big dance number…


    • On a more serious note, there are two parts to “cool” in my mind. The first is that “cool” is in the eye of the beholder, just like beauty. The second, as presented in the video above, is that anyone can “be cool,” just like anyone can be dramatic. It can be conscious or not. It can be most of time, sometimes, or never. But in the end, everyone can be cool.

    • Andrea Raymer


  • Amy Mills

    I dunno, I find the chase rather fun and life-giving. Nothing makes me feel more empowered than when I dress up for a night out and my boyfriend/best friend/sister looks at me and says “you look so cool.” gratification need not be made on a societal level…

    in any case I don’t think it’s the hedi slimane aesthetic that makes all those skinny rockers “cool” – but it may be the restlessness and constant hunger to dwell in the margins of society that lends them that image. it’s all attitude imo

    • Leandra Medine

      but it may be the restlessness and constant hunger to dwell in the margins of society that lends them that image ^^ definitely part of it, and something I did NOT expound upon, the correlation between punk and cool, right?

    • bamboodread

      You have such a cool face Amy! 🙂

  • Babs

    There’s always been the style I have and the style I want to have. Every time I purchase a delicate blouse in attempt to be “pretty and feminine” it ends up at Goodwill 2 mos. later. As you say, it’s about acceptance, and apparently I must accept that I am manly to the core.

  • tmm16

    Ha! I loved the end to this. I chuckled because I’m 22 and my current saying is “fake it till you make it,” so maybe at 24, it’ll be “swag”. I’ve had similar thoughts around what it means to be cool, and my take is “cool” is just a state of mind and usually those who we think are cool don’t even categorize themselves as the word. I agree with Lanatria – “cool” is just a state of being, and arguably just one acting out their truest self and maximizing their full potential because of it.

  • Julie Meowmeows

    My favorite musician if mf’ing Phil Collins. I couldn’t be cool if a cool asteroid from the planet Coolatron hit me in the face.

    • Angie D’Armetta

      god I love Phil Collins. I totally agree with this. I realized I couldn’t hang with the cool kids anymore middle of high school just couldn’t keep up. My favorite musician is Stevie flipping Nicks and as I type this I’m wearing striped socks up to my knees under my jeans

  • omg i love this.
    i relate so much.
    but ive come to the point where i dont care so much about being cool because ultimately what feels good is just doing what feels good, if that makes any sense, which for me is stuff inherently not cool at all, like talking about the environmental impact of carnivore diets or getting crazy excited about reading material and trying to discuss with everyone.

  • Michelle

    To me cool is confidence. Its a state of being okay with yourself. Confidence is what draws other people to you. Kind of a catch-22 to being cool.
    I find it so overwhelming to try and impersonate other people’s cool looks. So many people to me look cool. I try and copy one look and when I have that look I find another look like I like even more. Its exhausting.
    I think that me now, at 28, has started to accept the fact that I can’t compete or be everyone that I think looks cool. If I’m confident in myself then I’ll look cool to someone else, just like I think someone else looks cool.

  • Brooke Ireland

    V in line with your new years resolution! Possibly best resolution follow through ever.

  • Andrea Raymer

    I realized in the past year that I would much rather be a nerd than be cool. I used to spend a lot of time with someone that was constantly chasing “cool,” the aesthetic, the attitude, etc. Then I realized that I had never seen them excited about anything. In the quest for “cool” this person had foregone any sense of passion even about the things they loved the most. that is not a way i want to live. I like crying at every movie I see. I like getting freakout excited about things (I’M SEEING HAMILTON IN 12 DAYS GUYS!!!!). I like dressing like I am in costume. And any mention of me being cool makes me feel completely out of place.

    • Leandra Medine

      I’m with you! And when you accept that stuff, doesn’t everything just feel…feel…EASIER?

    • tmm16

      I also knew someone like this. She wanted to be “cool” so bad that she had no real identity, no self purpose, no uniqueness, and it made her utterly miserable. We are no longer friends because I just couldn’t deal with her insecurity and consistent chase for “cool”

    • Mariana

      For what it matter, for me being nerd is cool! 🙂
      Just like you in the excited-about-things-department, that’s when my inner 5 year old makes an entrance and I can’t shut up and I become restless.

  • Fran

    Just today I found myself feeling very self conscious in a social situation, looking at other girls and wondered how they could look so non-chalant and cool and I wished *I* was cool. It’s not something that I think about often, but today I did. So thank you for reading my mind and giving just what I needed to read, as usual!

  • Lísa Attensperger

    I love how many of the commenters are connecting cool with some kind of confidence and acceptance in yourself. I was just having this conversation today with a coworker, about how she now in her late twenties is coming closer to accepting/ knowing who she is. Now I’m thinking maybe feeling/ looking cool is connected to that feeling?

    • Leandra Medine

      You know, I’m finding that being 27 SUCKED because I became so obsessed with self improvement but conflated wanting to improve with needing to become a different, better version of myself as if the current one isn’t good enough. then a veil like, lifted when i turned 28 and i just said, fuck it. i am who i am and how i am and for as good as it is to try to do good and be better, it’s also wonderful to accept yourself for your flaws and perfections, embrace them and appreciate them, etc.

      • Mariana

        It’s the 27 year old curse! Do you know about The 27 Club, how that number of musicians died at the age of 27? That age wasn’t the greatest for me as well, but HEY, at least we managed to survive!!

      • Lísa Attensperger

        I guess we all go through what you describe at some point in our lives and maybe it is as soon as we realise that we cannot, will not change that we are able to move on. I’m looking out for that magical 28 though!

      • Mika M R

        At 27 I was being a mother and all that previous “Am I cool? Am I improving myself? Maybe I am not cool?” was swept away with milk coming out of me and a little gremlin whilling to eat me. So, yeah… I did survive. And I can give less than a f’ck if I am cool or not, I basically try to be a good person. Baby steps.

  • Julienne Lange-May

    The only cool thing about me as a kid were my clothes. I had moved several times and was very shy. I wasn’t hideous but remember thinking that I was so boring from the neck up and boring all way around. We lived in a small town but every Thanksgiving we would go up to Chicago for the weekend and literally buy everything we owned and wrap it up for Christmas. That alone may have warped me but when I showed up to school with my white crinkle patent leather boots, clogs, poncho or whatever “fashion” was at the time – it did give me a boost – a feeling of what you referred to as “je ne sais quoi”. That carried me through quite a lot of marginal days and yes – people did compliment me on my “cool” clothes and that made me feel good. I seem to have done the same thing to my daughter. She told me once- “Mom- everyone thinks we have money because of my clothes.” And yeah- I scrounged and made sure she did look fabulous as possible in preschool, grade school, every school. But somehow it worked right with her. She never worried or obsessed about clothes – and why would she when I made sure she had the right stuff. And one day in High School I dropped her off and she waltzed into the school dressed in her PJ Onesie for some “spirit” day event. I looked around and saw literally no other kid dressed up. Thoughts of Sue Heck from the Middle swelled up-and the accompanying humiliation. I wondered how is she so confident that she can do this?! And it occurred to me that something inside her was so right that she didn’t care! She just did what she did with no thought to what other kids might think or say. It was really the coolest feeing I ever had to have raised the exact opposite of me. I like to think it might have been the clothes- but probably not. Sue Heck is pretty cool right?

    • Claudia Cristina Deveze

      OMG! what a beautiful story! <3 From what I'm reading it seems that you raised a beautiful human being and that's so COOL!

      • Julienne Lange-May

        Yeah she is ultimately the coolest and uncoolest kid I know. 🙂 And wow I get “wordie” when I am snowbound for a few days. Cheers from PDX!

  • I think you’re pretty cool, Leandra!

    Is that not cool to say?

    • bamboodread

      I think you are way cool Kayla. And also everybody on this page who are giving their heartfelt

  • Lori Therrien

    Pretty sure when one is completely okay with exactly who and how they are, they’re cool. : )

  • dricous

    How are you not cool? Best stylist, funny and honest writer and podcaster. But I totally get what youre saying, Im 30 and its been 2 years since I also accepted my uncoolness and Im absolutely cool with that. Im free! I can do whatever I want.

  • When I was younger, cool and popular were synonymous to me. Now I’m 24 and I think cool is in the eye of the beholder, and it’s just synonymous with things I like. Maybe the person above me thinks all the things I think are cool are lame. But whatever, we’re all entitled to our own opinions.
    That being said, I do identify with the ‘cool girl’ style – I love me a good leather jacket. But that’s really just because I don’t like myself in anything else. I’m small and have a baby face so if I wear anything too girly/feminine I feel like a 5 year old. And I’m not into minimalism or gangsta urbanwear, so yeah.

  • Diana McNeill

    omg you’re only 28 what am i doing with my life

    • Donna


      • Ana Vla


  • Delaney

    I think that obsessing over trying to be cool will only make you look uncool, which is probably a pretty well-known principle. It’s hard to do when you are someone who is constantly aware of your physical, mental, emotional, and environmental states at ALL TIMES (i.e. me). Really, this sought after “cool” characteristic happens when you let go of the desire to be. You make yourself cool when you embrace your own individuality, and put it out there too.

  • Meg S

    I find that I’m at my coolest when I’m being myself. My dorky sense of humor, making jokes even when I don’t mean to, embroidering everything, absolutely loving pink while not wearing much pink at all, buying weird things for my kitchen (I really did need those whale shaped measuring cups, I swear), having a really diverse taste in music and an overwhelming urge to talk about all the weird podcasts I listen to if someone will listen. I’ve stopped apologizing for all of these things, and have embraced them instead. Never been happier.

  • meme

    I don’t know what cool is, but whatever you are selling Leandra, I’m buying.

  • Mia

    In elementary school I was dying to be part of this group of girls who always wore purses on the playground (big deal because uniforms) and in some way they even managed to have “cool” mannerisms. I think I tried it for a few weeks and started to feel silly, eventually finding myself in a boys’ kickball game (duh).
    Now here I am at 25, a complete minimalist forcing myself to wear outfits I’m incredibly uncomfortable in. I need to harness my inner child and just go with my gut. If I was speaking to my ten year old self she’d tell me to go throw on some overalls.

  • Anna

    If you had been that super laid back person, you wouldn’t have made it this far probably.

  • Kay

    Sorry in advance for nerding out: If you really want to dig into “coolness” re:relaxed face, consequence-free vices (smoking), etc, what is really being elevated is privilege: success without effort, vice without consequence, a physically expressed assurance that one has no need to try, everything just comes to this cool person with no struggle. The coolness of punk is the subversion of this, which while it also hinges on “not trying”, instead embraces the consequences of vice, rejects success and everything that displays it, and says idgaf about participating in the privilege competition, but everyone should admit that there is one. Punk is a little nihilist in that it only tears down a system without being an alternative, but this just further allows punk to claim the “not trying-ness” of privilege on its own terms.

    • Not Playin Witchu Piggy

      Excellently written.

    • Wow this was a super interesting take on the subject. It seems so obviously right but I had never considered it this way before
      Whiskey Tango Flat White | A body positive lifestyle blog

      • Omg just explored Whiskey Tango Flat White and it is now my favorite thing, I am worshipping you from afar Maddie!

        • Wow thank you so much Emily! I’m just kind of experimenting with trying to write about random things as interestingly as I can so thank you for the encouragement!

          • Get ’em superstar!

          • Leandra Medine

            This was so much, dare I say, cooler than learning in a classroom. Thanks for sharing it all on here ppl

    • ais

      such beautifully written insight. thanks for sharing.

    • Yue

      This is a fantastic comment, although what I feel about punk is that the line dividing between it been acceptable or not is often one of race and class. After all, punk is a choice and to make the choice you have to choices. My self presentation is rooted in respectability politics and I am very conflicted about it, but also this is the price I pay. And “embracing the consequences of vice” sounds nice but I doubt a plus size woman would be called punk (not to say that being plus size is a consequence of vice but in our society it is seen as one).

      • kay

        yes!!! it’s so rad you said that punk is a choice! it is one of the things that make it a rejection of privilege, which is not a choice. punk is def a commitment, at its most extreme to dying young, but it’s open to everyone who is willing to commit to really not giving a shit. I think I’m not understanding what you mean about being acceptable or not having a choice to be punk? not acceptable to your family or an employer you mean? or that other punks wouldn’t accept you? punk def doesn’t take money, its origins were the destitute of the UK and it has many traditions for avoiding the need for money. if you’re interested, idk if they were the first but john waters and Divine linked punk to plus size women specifically. the movie hairspray is so good! altho i would say john waters version of punk is a very cheerful american version where there is hope instead of nihilism. beth ditto is also living life in this vein. I’m going to look up respectability politics rn!!

    • ricotorpe

      Jesus H. Christ! Is everything about privilege? I recall many black kids from school who were cool, even those who didn’t have well-off parents.

      • Heather Chambers

        There are a many kinds of privilege that aren’t racial.

        • ricotorpe

          So what privilege does a poor black kid have?

          • Heather Chambers

            Well, you mentioned that they’re poor, so that rules out economic privilege. They might have heterosexual privilege. They might have cis privilege.
            They might have male privilege.

          • ricotorpe

            Your argument about privilege is simply inane. To you, somehow, the oppression against a poor black male isn’t that big of a deal if he is a straight male. I’m sure that will reassure him when he is harassed by cops… for the 6th time that month.
            Do you even think about what you believe?

          • Heather Chambers

            Quite a bit.
            I never said that the straight cis-male privilege our theoretical poor black (boy? Man? It seems to have changed between your comments) has outweighs the oppression he faces for being black.
            I never said it wasn’t a big deal.

            We were talking about the concept of coolness being tied to privilege, which you rejected on the grounds that it would mean a black kid, because of their lack of white privilege (or economic, you did imply that with “even the ones without well off parents”), couldn’t possibly be cool and you knew cool kids who were poor and black.

            I was just bringing up that there were other possible forms of privilege.

            I made no comparison value statements about thalose privileges and their impact on anyone’s life re: their other oppressions.

            It’s called intersectionality, dude.

          • ricotorpe

            It’s called bloviating. You weren’t contributing anything to the argument about whether coolness necessarily flows from privilege.

            I’m so sorry that the examples I mentioned (Otis is not “theoretical”) were not sufficiently intersectional for you.

            Maybe this will help. I saw a documentary about prisons, and it featured a prisoner who was being released from a male prison in Florida. He was black and flamboyantly-gay. Nothing was said about transgender, but he liked “girly” things, and when he arrived at the bus station, he called home and told his sister to tell everyone, “the bitch is back!”

            Because his record included multiple prostitution arrests and convictions, and his family couldn’t afford to pick him up at the gate, poverty is reasonably inferred. That may not cover every dimension, but this is a person who did not have any privilege to speak of.

            Nonetheless, this was one cool cat.

      • kay

        such a good point! Black cool is neither privilege nor punk, it is different. i could get into what i think it is, but i know its been studied and other people might know this better? and i do think privilege really shapes almost everything. obv it’s not the only big influence, but humans have put our stamp on most things in the world, and making hierarchies of power has been very important to us for a long long time.

        • ricotorpe

          Is it “different but equal”?

          • Kay

            What would you say?

          • ricotorpe

            No and yes, respectively. There may be cultural differences, but not always. Regardless, it boils down to charisma and social skills

          • kay

            you are saying both white and black coolness are based on social popularity, and social popularity is based on your ability to get people to like you, is that right?

          • ricotorpe

            Social popularity is part of it, so I oversimplified. We have to remember, as the OP said, the definition is hard because it has a je ne sais quoi nature. Also, would you agree the “ability to get people to like you” w.r.t. cool is probably better described as a quality that makes people like you without effort on your part?

            Being likeable is a sine qua non of cool, but it isn’t the only element. From my observations of people from different racial and economic backgrounds tell me that cool is heavily based on interpersonal personal skills. I have seen “black cool” as being different from “white cool” only in subcultural factors, but they seem overshadowed by a common “C” factor. (Yes, I made that up.)

            If we take Trump as an example, he has a strong personal presence, and for some, charisma. However, even overlooking the awful things he says and has done (ex: shafting subcontractors), the childish and obsessive butthurt he displays whenever his ego is bruised (or not stroked to his satisfaction) is patently uncool. The only people who think he is OK are the partisan nutballs who quasi-worship him.

            Obama, on the other hand, has real cool. Claims of Fox & Friends notwithstanding, he was a popular president. It is odd that I recognize his cool and feel the charisma when he speaks even though I despise him. (The final straw was not doing anything about the domestic spying after it was exposed by Edward Snowden.)

          • kay

            this is really nerdy again, sorry. it seems like your sense is that cool involves an element of being earned (“interpersonal personal skills”) and unearned (“quality that makes people like you without effort”). this is really interesting because it ties in with american ideas of meritocracy, that power can be earned, and then enjoyed freely bc it was “paid for” with whatever valued contribution was made- for social popularity that valued contribution is usually entertainment of some type, but some people are valued for their genuine friendliness and collaborativity- either way, these take effort. a social popularity meritocracy makes room for the ascension to power this way, but it’s still a hierarchy of power, with influence as the privilege at the top. in theory, a competitive meritocracy is more fair than most systems if the power is allowed to change hands freely, but of course life is pretty good at the top where everyone listens to you and cares about you (this is privilege), and it’s so much easier to put a few obstacles in the way of challengers than to yield fairly and have to work your way back up. in fact, there is a strong theme in american culture that approves of using influence to fight unfairly in the name of being scrappy, and using every tool available to compete at the highest level you can reach. this thinking sees fair play as “not fighting for yourself”. thats a whole other essay ugh sorry why. anyway, my point is that the cool of social popularity, though it might take effort to reach, is the privilege of influence, and influence does get things without effort.

            competitive meritocracy is usually billed as a racial equalizer, and to the extent that it sort of works, it can be. but there are real limits on how well it works for Black people in particular. it’s interesting that you bring up social popularity as an equal racial playing field, bc entertainment (not hollywood tho) is one place where Black people have been more allowed to compete on merit. even so, the US manages to award social popularity to Black people and still limit their privilege of influence, for example the tolerance for athletes’ political activism is not great, i.e. they are approved to influence fans to buy sports drinks, but not to call for police justice. even when Black people win meritocratic privilege, that privilege isn’t allowed to challenge the privilege of whiteness.
            your examples of obama and trump are awesome- trump so obviously began with a lot of privilege, and obama so obviously did not. fascinatingly, they each act as if they had the opposite- trump acts like a guy who doesn’t have enough and is eagerly grasping for more, obama acts like a guy who needs nothing. trump is agressively approval seeking, obama is assured and condescending. i think this is what you are talking about as how obama seems cool, and trump doesn’t. i do see a link to effort, trying vs. not trying- trump’s constant grasping is try-hard and not cool, obamas condescending reserve is very idgaf, very not trying, very cool. obama has, trump wants. this is a reflection of the privilege/coolness thing- coolness is still associated with freedom from need, and uncoolness with neediness, and the general real world relationship between privilege and need is obvious. why and how they up-ended it is fascinating and i could talk about it forever, but my point is even these examples reflect the connection between privilege and coolness.

          • ricotorpe

            If you are hell-bent on forcing everything into your mindset which reduces everything to privilege, I can’t stop your foolishness. Maybe you will figure out that there are other aspects which come into play. Until you realize that, your worldview will remain both limited and flawed.

    • awake

      please go eff yourself with your privilege word. furthermore, i deem you now and forevermore (until you get a clue) hopelessly and most definitely UNCOOL.

      • kay

        so you’re saying theres a chance 😉

        • awake


  • Fran

    You nailed it. The essence of cool: being comfortable in your own skin and not caring what anyone else thinks (about issues of style, anyway). Whether or not anyone else thinks it’s cool is then both random and irrelevant.

    Official coolness reminds me of the so-called “popular” kids in middle/high school. “Popular” in quotes, prefaced by “so-called”, because how many people actually liked them? Things that are officially cool are probably already on their way out, no longer cool with whoever is actually cool.

    ‘Model-off-duty’ looks look cool on models because they’re so gorgeous that it really doesn’t matter what they throw on and whether or not they run a comb through their hair. On me (sixty years old and not remotely resembling a fashion model) the slightly scruffy look would read as ‘bag lady’ rather than ‘model off-duty’. But I would still love to find a motorcycle jacket that would accommodate my big boobs in a flattering way. And who doesn’t like boots? They keep your feet warm and feel comfortable! Too old to wear jeans with rips and holes that I didn’t put there myself in the course of living. Pre-distressed jeans just feel *wrong*.

  • You are so cool when you do not care about if you are cool or not.


  • Audrey Fromson

    There is a nuanced cycle of cool, as told by Malcolm Gladwell in his 1997, “Coolhunt.” http://gladwell.com/the-coolhunt/
    I identify others as cool if they’re following their instincts, and have a personal justification or inclination for what they’re up to, who they’re listening to, what they do on the weekends. I think that with the concept of coolness, there is a respect and admiration for people who do things that fill their soul, and who do so unapologetically.

  • the fox forgot

    I’m 27 and I went through the cool thing hardcore in my teens. I spend a lot of time on the internet and spent all my money on music, music magazines, clothes, and hair products. I just wanted to know all the music. I thought cool was what I consumed or heard or said, and that opinions were important. I lusted for adulthood so badly.

    I do know I am cool now, because I have done the internal work on myself to be relaxed and not freak out at stupid shit. That’s what cool means to me now a days. It’s not being afraid to make eye contact, having a unique charisma, and being confident in your choices. It’s about picking out clothes that fit and being so comfortable in them, you forget they’re on. It’s about making people feel comfortable and heard and respected, which is ironic because I used to think cool was about being aloof and above the average person.

    Don’t be fooled by youth culture. It’s just a money making machine. If you’re cool, you are savvy to the cycle.

    Mother Nature may insist on taking your youth, but cool can go on forever.

    • Jessica


  • Stephanie

    My dad always told me that i should aim to be “warm” instead of “cool”- cause then at least you care about something.

    It’s interesting– there’s something incredibly distant about being cool. You’re untouchable, you’re elevated, and kind of better-than-anyone-else. But what I’ve been considering as “cool” as of late is people wanting you to be around. Not just being popular, but cool is being able to engage with as many people as possible. It’s about caring, being excited, being passionate… Giving a fuck is INCREDIBLY COOL.

  • Kathy Cappa
  • The whole cool vs effortless distinction – exactly! Fast fashion trends come and go and that’s fine, but dressing cool is all about feeling comfortable and cool and as a result, you emit that confidence to those around you. And this also applies to who you are and what you stand for – you just need to care about what’s important to you and not things because you think they make you seem cool. Whether that’s applied to your clothing choices, job, what you study, your interests etc.

    Not the easiest thing to do, but getting comfortable with who you are is what it’s all about, dressing in what makes you look and feel good, and whatever else it is that gives you confidence to as cheesy as it sounds – love yourself.

  • Christina

    I think you’re cool Leandra.

  • I kinda get this but also kinda don’t… I’ve always been so so fucking uncool I knew I could never be cool so I never bothered trying and embraced my weirdness and passion.

    AND smoking is not cool. I smoke, it’s bad, it’s unhealthy, it makes your clothes stiiiiink of smoke and that is like the least cool thing ever. Don’t smoke kids.

    Amber Love Blog

  • Efua Odafen

    Lmao the laid back bit just killed me looool. I can relate to this on many levels

  • Jayne

    I am always wishing I were ‘effortless’ and I’m just not, I wear makeup and winged eyeliner almost everyday and that’s fine. Everyone is different and that’s what makes everyone cool – if everyone were the same and looked so how boring would that be. It’s way more fun being yourself, in that way you are different and I guess ‘cool’ because no one is like you.

  • Emily

    Love this – I’ve been pondering the same thing and my conclusion is that cool isn’t a quality – it’s the outsider’s perception. Cause first, cool looks different to each person and second, no one in the world actually feels cool all the time. When casual acquaintances tell me they think I’m cool – a complement to be sure – I just want to scream in their faces “ARE YOU SURE ABOUT THAT!???! LET ME SHARE WITH YOU EVERY THOUGHT THAT RAN THROUGH MY HEAD WHEN I WAS ON THE TRAIN THIS MORNING.” I’m fully convinced that most if not all people are a swirling mess of emotions, insecurities, and indecisions like 95% of the time. (The other 5% is after two martinis.) But since most of us don’t have stream-of-consciousness mouths, people will sometimes mistake a placid exterior for a cool interior.

  • <3

  • Miss J

    I’m glad that you pointed out that “cool” and “effortless” are two
    different things. In fact, they actually have nothing to do with
    clothes. While both can be translated to fashion and one’s approach to
    it, what these labels represent essentially, are one’s approach to life.
    When you have the funds for it, it’s easy to flip through magazines and
    acquire all that (and a bag of chips), whether it’s your wardrobe or
    furniture for your home. It’s like when someone walks into a shop and
    says, “I’ll take the whole outfit from the window!” That, anyone can do.
    “Cool” is the KK power couple, that always look like it took them 2
    plus hours to get dressed, or Mr. Bieber, who looks like he spent two
    days planning his outfit. Cool were (and still are) people like Kate
    Moss or Johnny Depp, who have always looked like it took them two
    minutes (or less) to get dressed. What it all boils down to is if you
    give a sh.t, or not.

  • Charlotte Dallin
  • Saskia

    I always liked to think that “being cool” had more to to with being comfortable with yourself. Of course this always started roughly at twenty – before, cool meant looking like the girls on or in magazines.
    But thinking about it, most of the people we – or at least I – deem cool (Kate Moss, Bowie, Mick Jagger, Caroline de Maigret, Tila Swinton..) seem not to care what others think of them but to exist in a perpetual state of being true to themselves and not giving a second thought about it.
    They might not always be fashionable, but they are always stylish in the way that they don’t follow fashion but set style. Same goes for vices. Kate is not cool because she smokes, but some consider smoking cool because Kate does it and looks dang fine while doing so.
    Before I ramble on I’ll finish this with a quote form Doctor Who (also really cool): “Being cool is not cool”, uttered to people who said his dancing was not cool but rediculous.
    Tl;Dr – let your freak flag fly, nothing is cooler than unashamedly being yourself!

  • Slushee

    Hi – I love how you address these issues!

    So, my two cents… being cool is about doing your own thing. Not needing the approval of others, a state that only comes from being your own bellwether for what you think is cool. Being at ease with yourself. In fact for get the word cool, cause that’s a by product that says across the board – not just how you dress, but all of it.

    You’re already cool cause you’re doing your thing. Worrying about it, hunting it – it’s the wrong way to go!

  • Michelle Bruni

    I don’t know Leandra, I think everything about your maximalism-self is cool. In an effort to not use the word cool as an adjective anymore (you’re right, we have more in our lexicon than COOL), I think it’s inspiring that you’ve created this community who doesn’t give an f- about looking a model off duty or fitting in for that matter. The past few years I’ve tried so hard to fit in while living in Paris, and it was literally exhausting. How liberating it feels to wear whatever the hell I want; I think cool equates to confidence. We all want to be the girl rocking a watermelon bag (don’t we??), and I think confidence is what shifts our mindset from “this isn’t cool” to “this is bad-ass.”

  • Cool is the most overrated thing a person could ever hope to be. Just be you, it’s way more fun 🙂

    • bamboodread

      That IS being cool

  • You stopped caring about being cool before it was cool to stop caring.

  • Chioma

    Anyone who uses words such as “heretofore” is cool in my book.

  • Lucille

    This is SO REAL for me. In the era of J Law cool (no shade to her, cause it seems like she’s really just doing her), I constantly have to remind myself that I don’t have to be chill about things that matter to me, and don’t have to be excited about things just because someone else says so. I turned 26 last week which is an age that no one talks about and that has absolutely no milestones attached to it. The lack of expectation is so liberating!

  • Concerned Mum

    I did not realize you were so young, Leandre. You always sound so wise, which I often conflate with being older, although being smart and funny and creative at any age also makes one wise. You are amazingly accomplished, and, yes, cool.

  • bamboodread

    The coolest person is usually the one who doesn’t give a fuck about being cool

  • Viktor Latukha

    Why is it in humor section?

  • Whitney V

    Leandra, I’ve always thought you were cool. To me, you’re cool coz you’re yourself and are not afraid of being expressive, speaking your mind, and wearing lots of colours. You’re as cool as it gets, and one can only hope to be like that too 😉

    Love from London,


  • Johanna

    I find more freedom in not caring about being cool.

  • hailey thompson

    LEANDRA YOU ARE COOL. Trying to be cool is the least cool thing you’ve done all along. -This is written by not the coolest fish in the sea but I know what I am and I’m cool with it.

  • Sarah Smith

    Wanna Be Cool by Donnie Trumpet & the Social Experiment (it has Chance the Rapper in it if you’re a fan) should def be the soundtrack to this

    Why do I feel so dang overwhelmed about thinking about BEING MYSELF? I love the bit where you just break it DOWN. I am who I am and I like what I like or what I dislike. If whatever it is brings me joy and isn’t hurting anyone else in the process I’m just gonna roll with it.

  • Rozena C

    Oh my gah Leandra are you on the end of a tin-can telephone speaking straight to my heart? I STILL try to be cool, especially since I moved to Paris five years ago where every day is Judgement Day. But the cool people here mostly don’t wear colors or prints and their hair is always stringy which is simply not my jam so about a year ago I decided to own it and yesterday a super-cool parisienne complimented me on my grandma’s very oversize stupidly purple hand-me-down earrings. Keep on’ keepin’ on, sister suffragette!

    • Holly Laine Mascaro

      Lol the opening sentence in this comment is amazing

  • Holly Laine Mascaro

    I HATE when people try so hard to be cool — we all clearly can fall into it at times but if push comes to shove, I value when others (and myself) embrace our weirdness and uniqueness. That’s what makes us cool, as cheesy as that sounds. I’m so sick of these pretentious people who clearly put so much effort into fitting a mold that they deem makes them “cool.” It’s so transparent and unoriginal, and it’s why I enjoy Man Repeller’s approach to fashion so much more than many other sites. Especially in today’s social media driven age where there’s constant pressure and comparisons to be made, it only results in feeling inferior, instead of just owning what you have that makes you YOU. Sorry I have a lot of thoughts on this lol.

  • gwendolyn

    The conscious chasing of ‘coolness’ in appearance and behaviour is essentially juvenile and insecure. The constant preoccupation with how you are seen by others is a privilege of puberty. It’s what you do when your personality is developing. Once you’ve left high school, ‘cool’ becomes meaningless, or at least changes its meaning radically. For teenagers, ‘cool’ is defined by strict rules, what you can’t wear, can’t do, can’t say in order to fit in and not be ridiculed. The irony is, only when you stop trying, you become cool in the original meaning of the (slang)word: calm, confident, individual and self-posessed. An adult.

  • Mace

    Hello! I just wanted to say that as a teenager stuck in a crushing and vicious cycle (of wanting to buy clothes I adore – being slapped in the face by self preservation – then buying clothes that are considered ‘cool’), this gives me hope that one day my flared jeans, fur-lined crocs and beret wearing dream future self (possibly paired with a mustard turtleneck) will finally be free. THANKYOU xx

  • Ami Savage

    Cool post!

  • Systemfive

    The fact you’re writing a blog post about not trying to be cool negates your entire stance on not trying to be cool. This is just another one of your phases/attempts at trying to be cool, by not trying to be cool.


  • HollyO

    If Leandra’s not cool, then I don’t even know the definition.

  • Lizlemon

    Want to drop in with another analysis of coolness being anti-privilege. But right before cool got entrenched into the North American lexicon in the 50’s cool was used to admonished then to praise. Black jazz artists used the phrase “keeping your cool” to reinforce resolve in the face of oppression faced. Hence Miles Davis’ The Birth of the Cool in 1949. Going back even farther cool’s meaning was still about resisting social pressure. There’s this definition from 1825 ;”calmly audacious”.

  • MarieClaire

    Great article! The funny thing is you are perceived as cool to so many people. Your weird and funny personality along with your own style Ian what makes you cool is my eyes. I think it’s great that you are out there being who you are.

  • Greta

    Why everyone is so obsessed of ”being yourself” these days ??

    • Leandra Medine

      THIS is a good question.

  • Julie Lopez

    OK. I might be simplifying this too much, but I believe there is the mainstream “cool,” which, as pointed out, is ever changing. And there is also “cool” in the eye of the beholder. To me, “cool” is about feeling comfortable with yourself regardless of who you are, skin color, what you are wearing, etc. That I crave and do what it takes to achieve it, whether it takes changing something on the inside, or just wearing more comfy shoes ,:-p

  • John Tracey

    I am trying so hard not to be cool that II must be cool

  • Mar

    I think that being cool is being yourself. I always thought of you as a cool person. Not so much because of your clothes, or the fact that you live in NYC, but because I see you as someone who shows up as herself. Someone who is able to laugh at herself, has her own ideas and stays true to who she is. To me this is cool as fuck.

  • This speaks to everything I am. Grew up always one head taller than everyone else, was (am?) constantly obsessed with attaining coolness. I’m slowly accepting that its never gonna happen. I am who I am, a tall awkward maximalist who loves experimenting with clothes and more often than not trips up on my attempts. But hey, I’m learning. 🙂