Am I Too Old to Be Cool? The Paradox of the Aging Hipster

Feeling old comes in waves. I remember turning 23, repeating that classic, petulant Blink-182 lyric on repeat in my head and honestly wondering whether I was “done” because I didn’t feel like going to a party that night. Yikes. But in a way, I was. The styles I’d adopted up to that point became harder and harder to deviate from, the bands I loved then largely remain my favorite bands eight years later. Partly because hipsterdom won, and everyone dresses pretty nicely now. But the adage attributed to the late comedian Lenny Bruce, that “there’s nothing sadder than an aging hipster,” would start ringing in my head from then on. Don’t be that guy. But it’s tricky striking that balance between staying true to your cool self and not making a fool of yourself doing so.

There were other milestones of irrelevance to come: Being called “the adults” by a younger guest at a New Years party thrown by a friend and his 21-year-old sister; speaking to a teacher friend’s middle school class (a notch on the oldness belt itself) and being asked by a student why my shoes were dirty. “Umm, don’t let the J Crew button-up fool you. I am punk fucking rock, kid. I was banging out Buzzcocks covers when you were in utero—oh my God I’m that old guy now, fuck.”

And I’m far from the worst culprit in my cohort. There’s the aging skater still lurking around skate parks and dive bars hiding behind their beanie and Pabst. The aging biker spending too many weekends getting ‘grams in Joshua Tree with their rotating cast of would-be bandmates. Add to that the big city corpo guy with the ever-expanding record(/toy/video game/weed) collection and ever-shrinking pool of people with whom to enjoy them. Hell, one friend has belatedly fashioned himself into an ad hoc SoundCloud rapper, complete with color-dipped braids, and gets called “Lil Pump’s busted ass dad” all day on the internet now.

But who cares what all the cool middle schoolers think? (To be clear: Everyone.) James Murphy was 37 when Sound of Silver came out in 2007. Andy Warhol was 34 when The Factory opened in 1962. Killer Mike and El-P were 38 when the first Run the Jewels album dropped. Lenny Bruce may have been right that it’s harder for the hip at heart to age gracefully, but then, what if they don’t age at all? It doesn’t matter that James Murphy is pushing 50 until he stops making wonderful art. We’ll go see a 52-year-old J Mascis shred out a Dinosaur Jr. show with long hair and Vans, no questions asked. And make no mistake, all of these icons could never have been so cool in their twenties. It took experience to get there. There may be nothing sadder than an aging hipster, but there may be nothing cooler either.

So no, you’re not too old to be cool, but you may be too irrelevant to be cool. If you’re not backing up whatever fashion statement you’re making with an equally contrarian lifestyle—be it in your day job, your side projects, your activism—you’ll end up being that thing the real cool kids can sniff out like a bag of Flamin’ Hot Cheetos: a poseur. But to be honest, even cool middle schoolers probably didn’t understand James Murphy or Andy Warhol at the time. They probably got Run the Jewels because everyone understands good hip-hop, but you get the point. There are cool middle schoolers everywhere in life telling you your shoes are too dirty or you need to dress your age, to stop pretending you’re a DJ or stop wearing Vans. And maybe they’re right, but they’re just afraid of the proverbial high school to come, that they too will age out of coolness, maybe before they’ve even found it.

Show them there’s nothing to be afraid of. Be that guy and be him proudly. Or if your getup is feeling a little infantilizing, switch it up for a more classic look. It’s the second guessing that’ll do you in. Don’t take it too seriously and keep having fun, and you might even end up being that other that guy: the Cool Old Guy. Could be worse.