On being cool

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?