Geezer’s Paradox: Not Caring is the New Cool

My friend Jack recently offered a retrospective on his decade-long dalliance with sneaker trends—a ride as unpredictable as it was swift. He began faithfully attached to New Balance, those once-maligned “dad shoes” that screamed suburban resignation. Then came Converse, adopted not for comfort but for credibility, as his children entered the age of judgment and he entered the age of trying not to embarrass them. Shortly thereafter, he flirted with On sneakers during a Lululemon-inspired phase that boldly declared, “I’m trendy, indeed!” Yet as fashion’s fickle currents swept him toward HOKA’s cloud-like comforts, Jack eventually circled back to a reinvented New Balance—now celebrated as a bona fide streetwear icon. Worn out by the relentless trend chase, he abandoned the pursuit of cool, discovering—ironically—that true style springs from indifferent authenticity.

Jack’s quest for sneaker coolness, while amusing, is not merely anecdotal. It exemplifies what might be called the Geezer’s Paradox: the older we get, the less we care about being cool—and, perversely, the cooler we become. This isn’t wisdom. It’s exhaustion masquerading as enlightenment. The effort required to stay ahead of trends eventually outweighs the social reward, and so we opt out. Not with a bang, but with a sigh and a pair of shoes that don’t hurt our arches.

The paradox lies in the cultural feedback loop. Indifference, once a symptom of age, now reads as authenticity. And authenticity, in the current economy of curated selves, is the ultimate currency. Jack didn’t become cool by trying. He became cool by ceasing to try—though not before spending several hundred pounds on footwear that promised transcendence and delivered blisters.

Idea for Impact: Coolness, like happiness, resents pursuit. Stop chasing it and it might just follow you home. Or at least to the corner shop in a pair of sensible trainers.