On being cool

alexa chung

I have never felt cool. Not as a teenager, and certainly not as an adult.

I've made many attempts towards achieving coolness. In junior high I was convinced, absolutely convinced, that if I had a pair of Guess Jeans I'd be cool. In my grade, flashing that iconic triangle on the back pocket of a pair of slim-cuts marked you as a higher echelon of teenager. It practically guaranteed your admittance to the popular kids' table at lunch and earned you a slight nod of respect from the girls who sat there. Though I begged and pleaded and swore that IF I DO NOT GET A PAIR OF GUESS JEANS I WAS GOING TO DIE, LIKE SERIOUSLY DIE, I knew deep down that owning those jeans wouldn't necessarily make me cool.

When I was a kid, I had a babysitter who was cool. She had blonde feathered hair and a Trans Am and a gold necklace with her name imprinted in curling script. I think her name was Jennifer. Jennifer had a college boyfriend who would sneak in after she thought my brother and I were asleep. She didn't care an iota about being caught, and when she was, expressed no surprise or regret. I wanted, with all of my being, to be Jennifer. Jennifer possessed a nonchalance about being cool that only cool people seem to have. It took me a long time to understand that this nonchalance was what made her cool in the first place. She didn't try at it like I did, with my desperation for Guess Jeans. She just was.

It seems that everywhere you look, people are trying to be cool. They're dying their hair psychedelic colors or shaving off one side. They're buying neon leather messenger bags, and vintage Vespa scooters, and expensive sunglasses, and tee shirts with mustaches on them, and basically anything from Urban Outfitters. Myself included. Some people, the lucky rich ones or those with good credit, spend hundreds of dollars on clothes they see in fashion magazines all with the intent of being cool.

In Silicon Valley, some tech entrepreneurs have become enamored with with socks. The New York Times reported last week that flamboyantly colored, wildly patterned socks have become de rigor among those looking to be a part of the in-crowd. “I have been in meetings where people look down and notice my socks, and there is this universal sign, almost like a gang sign, where they nod and pull up their pant leg a little to show off their socks,” said Hunter Walk, 38, a director of product management at YouTube, whose favorite pair is yellow, aqua and orange striped.

In the classic movie Grease, Sandy, poor poor good girl Sandy, instantly became cool when she abandoned her cashmere sweater sets and mid-calf circle skirts for a skin tight pair of black vinyl pants and off-the-shoulder black tube shirt. That's when she got the guy, and cemented her status as pink lady. That's when she became cool. I remember sitting, rapt, watching Sandy strut confidently throughout the high school carnival. She was a goddess.

I wonder if a change of clothes can really make you cool. If I buy a pair of skinny cords at Madewell and ankle boots, will I get one step closer to channeling Alexa Chung's charming quirkiness and model-quality good looks? (Inexplicably, Alexa Chung seems to be the personification of cool girl these days - there's an entire Tumblr dedicated just towards being her.) If I drape myself in one-shoulders jersey maxi dresses and floor-length furs, will I tap into Bianca Jagger's chic demeanor? Men don't seem to have this quandry. Men want to be like Johnny Depp, who looks like he crawled out of the gutter most of the time, scraggly bits shedding from his oversize leather jacket, scraggly facial hair sprouting from his chin. Or they want to be Clint Eastwood, or Marlon Brando - men who look as though they'd rather get into a knife fight than step into Barney's.

The Times article notes that techies purchase wildly patterned, garish socks both as a way to impress coworkers and as a rebellion against their typical boring uniform of khakis and sweats. Socks are a nod to fashion without appearing as though you are playing by mainstream rules that Silicon Valley shuns - like, heaven forbid, dressing up. Going deeper, Diana Crane-Herve, emeritus professor of sociology at the University of Pennsylvania, said workplace fashion fads like outlandish socks are often an unconscious way to deal with worries about job security or fitting in.

Throughout time, women have based their sartorial choices on the desire to be cool. But being cool seems to be mostly about impressing the peers in our gender group than anything else. They're the ones we look towards to define what it means to be cool.  If we pattern mix, or wear Madewell cords, or thrift, or get a tattoo, our cool role models might think we're cool as well.

So what do you think about being cool? Have you ever felt cool? Be honest - have you ever bought an article of clothing with the intent of being cool? Is coolness about social acceptance, or nonchalance? Do you think clothing choice is related more to being cool, or to expressing individuality? Do you have cool role models?


  1. Am I the only adult woman of my generation who doesn't find Alexa Chung extraordinary? To me she just seems like another NY hipster girl. I don't want to bad mouth her, but I really just don't get it.

    I tried to stop caring about being cool, but there are some times when I want to look cool (usually when I am going out). Along the same lines I have been in the company of people who make me feel uncool, but in reality I know I'm uncool. I just don't have the desire to keep up with the cool kids anymore.

  2. oh noes! I have pink streaks in my hair, ride a scooter and have a neon Cambridge satchel! What's funny is that with me seeing a neon lace skirt on the ASOS site doesn't make me think "wow look at all the other cool bloggers who have this skirt" it makes me think "it's like it's radioactive-it's so bright I love it" the same with the other things. I don't buy them to fit in or be cool--I buy them because I generally like them.

    I guess I felt cool in high school. I was the girl who was goth when no one was goth--or thrifting bright mismatched patterns and purposely clashing. I did it to be different--not to be cool--but it's a fine line I suppose

  3. Oh, I had those Guess jeans -- and they DID make me feel cool! :-)
    Of course, that was 25 years ago.

  4. Well, I'm in my late 20s and have no idea what Alexa Chung looks like. I recognize her name as somebody "important," but I don't know more about her than that. I watch copious amounts of TV, so it's not like I'm sheltered from the world, I just seem to always miss whatever everyone else thinks is cool.

    I was not cool growing up and any efforts to remedy the situation resulted in drawing attention to my uncoolness. In my mid-20s, I decided to live in a way that allowed me to feel like myself. I've been told that I'm everything from stuck-up to a b*tch by my peer group, but older adults or people who take the time to get to know me tend to think that I am confident and competent, if a bit of a loner. I would not classify myself as cool, but I would say that at this stage in my life, it doesn't matter as long as people think I am intelligent and skilled at my work. I aspire to feel confident more often than not, but am still working on that.

  5. I love how Brene Brown breaks down the idea of "being cool". She calls it an emotional straightjacket (see her post here: http://www.ordinarycourage.com/my-blog/2011/5/9/cool-the-emotional-straightjacket.html). Trying to be "cool" or "fitting in" is a barrier to true connection with others. As I mature, the idea of being cool has become less and less important, but being true to who I am is important. And if others think that's cool, great. If not, who cares?

  6. Its funny--- when I was young, being cool meant dressing like my friends.

    Today, I feel my coolest when I am true to myself.... clothing and whatever else!

  7. I love that article from the NY Times about socks. I've been wearing funny socks for years because it's something I can wear that is fun and no one usually knows unless my socks peak out. Now the Silicon Valley nerds are wearing them to look "put together" which is the opposite of why I wear them. Even now I'm wearing green socks with bicycles on them but they are hidden by my boots.
    I've never been cool but I've embraced it for a long time so it just feels right.

  8. For me, being cool has always meant taking risks; in fashion, and in life. NOT following a trend passed down by the New York Times.
    I was also victim to the crazy urgent need to own Guess Jeans in high school, but to me, there wasn't anything 'cool' about them - it was more to fit in - the opposite of cool, really.

  9. I try to pay very little attention to what is considered "cool" - not because I think there's anything wrong with trends or coolness or anything. Trying to be cool is a slippery slope for me. When I get in the "I need to be cool" mindset, I end up trying to be someone I'm not and feeling pretty bad about myself. I try to pick what I wear based on how it makes me feel. Does it make me feel pretty/beautiful/fun/sexy? Then I'll wear it! Sometimes the things I like happen to be cool; sometimes they aren't. I'm fine either way. As for Alexa Chung........that girl needs to brush her hair. She constantly looks disheveled which annoys the pants off me. My mom would be embarrassed if I went out into public and had my picture taken looking like I had not taken a brush to my hair. I hope her mom is okay with it......

  10. Maybe I'm a bit sheltered, but I have no idea who Alexa Chung is. Is she an actress or singer? I guess being in my 30s and spending way too much time absorbed in Teen magazines when I was a youngin' I'm out of touch with pop culture these days. But I can totally relate to you with that oh-so-coveted upside down red triangle! I had some Guess jeans and felt so cool. I guess growing up I never was part of the "cool" crowd, but just a plain Jane. Though I dreamed that one day I'd marry one of the Coreys (Haim preferably).

  11. I think those who are cool don't concentrate on being such. Cool can't be defined, or found in a pair of J Brand colored skinny jeans or a Cambridge satchel. Those who are cool may have such garments, but consumption does not determine coolness. While Alexa Chung doesn't do squat for me, I think she is seen as cool because she doesn't seem to be trying, she just is. I fear this land of fashion blogging that we live in makes women feel that coolness can be achieved by what they wear instead of who they actually are.

    I think we slightly older and wiser women can bring back the real cool - that Johnny Depp is cool not because he is disheveled, but HOW he makes it look good and effortless yet elegantly disheveled. How Sandy may have suddenly become cool with her cigarette and leather pants, but it was more because she took control of herself and her sexuality. That if our goal is to impress our peers we have already lost our coolness quotient, and that we know we're cool because we're confident and we're true to us. :)

  12. Alas finally finding a pair of Guess jeans at Ross did not make me cool. It was when I stopped trying to be cool by cool's terms and started being me, being a leader, and wearing whatever, my dad's cast offs, bright dresses from the 1 dollar bin at the thrift store, etc, that I started having my own cool with my own crowd, which was not the same cool crowd. But even now, it the random outfits I throw together from whatever I have (I pretty much have a stapleless wardrobe, it seems its the brights that don't get worn as often that make it to the thrift stores and clearance shelves) that clothe the cool I already am, at least cool to me and my friends. Being grown up rocks!

  13. These days, I do have times when I feel cool (yay!). I somehow have the ability to give off a "don't f*ck with me" vibe when I want to, so that's where it comes from I guess ;-) That wasn't always the case. In fact, I very vividly remember a jacket I bought with my mom when I was 12 years old. I wanted it and then never wore it because it was too cool. I feared the other kids would mock me for trying too hard. Looking back, that was absolutely ridiculous. It was the kind of jacket everybody wore, but I wasn't daring to fit in. So I think I was the epitome of uncool. I didn't even think I could emulate cool. Last year, a friend said she'd describe me as "tough and cool". I was super proud. I don't look the part, so it's a surprise to most people.

  14. I don't think cool has much to do with appearances. I work with blind teenagers and they told the other teachers that I am a 'cool' teacher. They don't see what I wear only what I say to them or really I just listen to them most of the time. I think coolness has more to do with a person's attitude about life.

  15. I think cool has less to do with what you wear than how you wear it. For example, someone could wear the exact same outfit as alexa chung or whoever, and not be able to 'pull it off'. I think 'coolness' is a mentality that one has to talk themselves into in order to project. just my 2 cents!

  16. When I was in the Navy, I used to rebel by wearing wildly-patterned,bright, usually argyle socks under my uniform. It was my way of knowing that I still had a bit of individuality, that "the man" hadn't taken complete possession of my body and mind. Now,when I'm not working (I wear boots and socks at work) I usually wear no socks at all - rebelling against, I think, my parents' insistence that I always wear socks, all those Navy years (12 1/2 years) of having to wear socks with boots, and still having to wear them when I work as a civilian.


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