What the f*** does it mean to be “cool” anymore?

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I have never felt “cool”. I feel out of place no matter where I am. I always feel either over or underdressed for any occasion. I often worry that I’m either too arrogant for the simple or too stupid for the sophisticated. I’m insecure in just about every situation I approach and I’m certain people will either be sickened by my apparent over-compensating, or I’ll be mocked for my general introverted nature and lack of confidence.

I’ve just never been sure what the trick is.

Back in high school and college, I at least knew what to shoot for, if only by process of elimination. It was always grossly apparent who the “not cool” people were.

And no, I’m not talking about the anime-loving, geeky virgins.

If you liked “top 40” music, watched The OC, shopped at expensive, mainstream clothing stores and didn’t have much of a personality outside of your favorite sports team, you were not cool.

We know, you thought you were cool, but that’s what made you so fucking lame and boring.

The cool kids therefore, were obvious. They played in bands, listened to music you hadn’t heard of and got piercings and tattoos. They were into art and probably hated that popular thing that you liked (because that popular thing that you liked was for fucking idiots).

They were progressively liberal, informed and open-minded, but also unafraid to offend; to live their lives, and let others live their lives, recklessly.

Have I actively tried to be cool? Or at least, tried to mimic people who were cool? Of course. Who hasn’t? But I also knew who my tribe was, who I identified with. I knew what team I wanted to be on.

Now though, I really have no idea what the fuck it means to be cool, and I don’t know who to side with.

I watched as the skater kids became emo, and then became “scene” and then slowly evolved into various hipsters.

And for a while, when hipsters still had muscle-head guidos, Abercrombie-wearing frat boys and a general “mainstream” to be counterculture to, everything still seemed pretty straight forward.

Hipsters were a general “fuck you” to those people who thought they were cool, but weren’t, and that made them the absolute coolest.

But then the worst possible thing happened. The hipsters actually won.

They didn’t just barely edge out the competition to become the new front-runners, either. Hipsters forced everything else into an unconditional surrender, where every other cultural niche was forced to adopt their practices.

Hipsters are not a cultural niche. They are our culture. Yours. Mine. That guy who claims to hate it (especially that guy who claims to hate it).

Everything hipster is completely mainstream. The fashion. The magazines. The music. The attitudes. And I can’t help but wonder if it’s all still cool, or if the people mocking it are cool, or if none of it matters anymore because it’s all just become the cultural equivalent of a snake eating its own tail.

Hating hipsters is now the most hipster practice imaginable.

Yes, there will always be two or more different groups who both see their lifestyle as the “cool one”. Rock vs. Disco. Punk vs. Metal. Indy vs. Pop.

But this is different. Because everybody is a hipster now, because the death of the hipster in the purest sense has caused its lifeblood to be soaked into every other cultural niche, we are now in a Hipster vs. Hipster war.

Are you a total douche if you only drink craft beer? But isn’t Pabst Blue Ribbon the iconic nectar of the hipster?

Where are we on tattoos, beards, good haircuts and plain (but stylish) clothes that fit properly? Are you cool now if you don’t adopt all those things? Or are you uncool because you’re trying just as hard to avoid that look?

Giving a shit and not giving a shit require the exact same amount of effort. Not picking a side is picking a side.

What about preferred entertainment? Being into grunge, folk, synths, 90s Simpsons, Seinfeld or the original Star Wars trilogy were once simple identifiers of one’s pop-cultural sophistication. Now? They’re the most yawn-worthy, cookie-cutter things you can possibly staple to your social media personality.

Is owning a Sega Genesis or an N64 cool? They sell them at Urban Outfitters and Bed, Bath and Beyond. Are you playing them ironically or are you actually that uncool that you truly enjoy them… which, I guess, would make you cool?

Then there’s Vice. The once proclaimed “hipster bible”.

Vice, as a whole, is more compelling than it has ever been. No argument to be had. But it’s also more mainstream than it’s ever been. So… is it cool to be into Vice still?

Politically, who even knows how to be counterculture anymore? It seems like the progressive voice is stronger than ever in North America, and that’s great, but politically correct leftists are rapidly becoming flat-out bullies and have us all scared of what to say, what to think and how to feel.

Your friend on Facebook freaking out over micro-aggressions is as uncool as the one who constantly posts pictures of their new Diesel pick up truck and statuses about how Obama or Trudeau is screwing up their respective country.

What is cool? Is it counterculture or is it counter counterculture?

I think we’ve come to a place where we need to accept that everybody is trying to be cooler than the person next to them.

We’re so overexposed to how amazing other people’s lives are through social media that of course we feel the incessant need to somehow prove we’re the coolest, if only to be skewering the next person’s inherent need to “feel cool”.

The only way to really beat the vicious circle, I think, is to just do whatever makes you comfortable, and be unapologetically into whatever sincerely turns you on.

Maybe that’s been the trick all along.

The only alternative is that we all just turn into the entitled, insecure, infantile, post-ironic, personality-void husks that old people already think we are, and there’d be nothing cool about that.

Chris