How To Be Cool

People’s definition of cool changes over time. In high school, the cool kids could be the obvious choices (the cheerleader and jock) but they could also include the aloof stoner chick who smokes cigarettes in the parking lot on the hood of her diesel Mercedes. Or the guy who dresses like a greaser and has a beautiful face—the kind of beautiful that isn’t valued quite yet but will be in a few years. To be a cool person in high school, you have to either care too much or not care about anything. The common thread, however, is being attractive. Being pretty is cool. This is especially true in high school because not everyone is attractive. It’s not like being in your twenties when everyone has pretty much caught up with each other lookswise. People either have nice faces when they’re sixteen or they don’t. And if they don’t, it usually just means that their face isn’t ready yet. It needs go back into the oven for another two years.

When you get out of school, however, the definition of a cool person becomes more vague. The aloof stoner chick isn’t really cool anymore because she’s done too many drugs and when you look at her face, it makes you feel sad. The jocks and cheerleaders aren’t cool anymore because they’re not allowed to be. They had their time under the sun and now they have sun damage. They have to go in the defroster for a long time.

No, being cool becomes more indescribable later in life. Sure, you have the nightcrawlers who get written up in magazines and attend fancy parties but they aren’t real to you. Their coolness is too obvious and exists in a completely different realm. In fact, they’re almost seen as uncool because they’re still subscribing to the idea that someone could be popular. Being popular when you’re out of school usually means nothing. It’s just for those who can’t give up on the idea of social ranking. Popularity is strictly for them and their piece of mind than it is for us. I mean, how is someone in the society pages of Interview going to make you feel bad about yourself at 25? Really.

The people who are considered to be cool in their twenties and later on are almost like your mentors or better versions of yourself. You see yourself in them but you think they got it right a little more than you did. Their jokes are better and their clothes are cuter. You study them with a fascination but not at a distance. The coolest person you know could very well be your best friend.

Humor becomes more of a valued quality. In high school, the funny kid always made people laugh but they weren’t necessarily popular. They were considered too fringe and became sort of a guilty pleasure. You laughed at their weird jokes but stifled them with your hand. When you get older, however, people laugh out loud and celebrate humor. Bitchy jokes usually aren’t considered cool though. It’s too easy to be truly mean and it reveals something unfavorable about the person who’s telling the joke, like they care too much or have weak self-esteem. Weak self-esteem is the enemy of cool. You have to own every aspect of your personality and poke fun at your shortcomings before anyone else can. Cool people give a knowing wink and nod to everything. They “get it” before there’s anything to actually get.

Aloofness isn’t really considered to be a cool quality post-high school but if you’re unconventionally pretty, you can be whoever you want and still be fine. Beauty that gives the middle finger to society’s standards (like Beth Ditto’s for example) will always be seen as “refreshing” and “cool.” It’s all actually done with a slight condescension but whatever. It still beats giving another compliment about Kate Bosworth.

A cool person is someone who possesses qualities you could have but don’t, at least according to you. Cool people are inspiring. They make you want to improve yourself in various ways. You know how people sometimes say, “Real cool people don’t know they’re cool?” Um, yeah, no. In this age of self-awareness, it’s impossible not to know how you’re being perceived. You just keep it under wraps! But the awesome thing about coolness as a less fragile young adult is that it’s designed to inspire rather than make you feel inadequate. Thank god because you really don’t need some hot cheerleader making us feel like crap when we’re thirty. TC mark

image – Jack Mitchell

Ryan O'Connell

I'm a brat.


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  • sb


    • Asdf

      Aloof story, bro.

  • guest

    this is one of the more !!!!!!!! things ive read on here in awhile.  way to articulate what we’re all thinking but never realized it, again !

    • Carmella Kaya Osborne


    • Carmella Kaya Osborne


      • Halie Smith

        I get it. He or she is saying that he articulated something we knew  but weren’t necessarily conscious of. Or would have been able to express. This is what good writing does.

  • mashka

    great job saying perfectly and succinctly what we (hopefully) are all thinking

  • Alina Trifan

    being uncool is the new cool.

  • Dutton Ivan

    this is someone’s view of what it is to be cool, but personally I feel completely different about it.

  • Guest

    So, if you’re ugly you’re fucked?

    • Aja

      Nope.  Being witty and charming trumps being attractive any day.  Easily.

  • Smokey Problemson

     I stopped at the first paragraph because I was actually a cig-smoking stoner girl with a diesel Mercedes in high school, and therefore (in my mind, as a takeaway from this piece) am cool forever. That’s the point of the story, right? Right.

  • Gregory Costa

    Don’t use a Mac.  Be a real man and use a ThinkPad…cool and professional.   

  • TuraLura

    Ha ha! You kids are funny. 

    Being cool isn’t really about being perceived as cool. It’s about the way you interact with the people around you. And it’s about what you do, as you go about your life.

    Truly cool people are understanding and tolerant of others’ points of view. They don’t get hung up on small, petty details but try to focus on big pictures. They refuse to rest at the point of popularity, in fact they may be indifferent to it. They’re just trying to do whatever it is they do in a cool way: without messing with the next person or being messed with. 

    Coolness evolves out of curiosity and skepticism, a sense of personal seriousness and dignity, and a willingness to challenge staleness, convention, conformity and apathy. 

    Some things will be cool forever. Some people will be cool forever. Here is a partial list:
    Having a way with words is cool. Being a fantastic dancer is cool. Having good taste in music is cool. Science is cool, so is bartending. Medicine is uncool (that is, being a doctor = uncool), unless it has to do with research or death (being a medical examiner or doing stem cell research = cool). DJing and being in bands used to be cool, but really aren’t anymore. Classic cars are cool; vintage guitars and vintage furniture are cool, especially if you didn’t pay too much for them. Having too much money can become a barrier to being cool, it definitely can’t make you cool. You can be difficult and still be cool, but meanness, bigotry, close-mindedness and cruelty are all totally uncool, forever. 

    People who will always be cool: Albert Einstein. Louise Brooks. Alfred Jarry. Richard Hell. James Brown. Tura Satana. The Shangri-Las. Thomas Merton. Miles Davis. Malcolm X. William S. Burroughs. Ronnie Spector.  John Cazale. Nicola Tesla.

    Now you know.

    • Kitty Sanchez

      Einstein was kind of a tool.

    • Guest

      You=not cool.

    • Your mother

      You are like one of those retards who sit in the cool people’s seat and don’t even realise it. #uglydumbbitches

    • Halie Smith

      Medicine is cool if you’re a woman. Female Doctor = Badass. Esp. if you’re into gynecology/midwifery. 

      • TuraLura

        You’re right.

  • Tau Zaman

    I think it’s spelled “peace” of mind.

    • Asdf

      Way to give him a piece of your mind.

    • mysticlipstick

      Re-read the post.. You’re incorrect. 

  • Tadeusz

    Oi, that’s a lot of pontificating on coolness… 

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  • Gretchgurl2003

    This is so fetch.

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