As I write this, it’s 3 degrees in Chicago and 18 degrees in New York. And what cozy streetwear hacks do I see from those avatars of cool style, teen boys? In addition to a squadron of Canada Goose jackets, which I love and approve of btw, I spy tiny beanie hats. And…I’m perplexed. After all, how does a knit cap that’s too thin and not even pulled fully down on the ears keep someone warm when the wind chill hits the negatives?
Teen Boys Are Obsessed with Miniature Beanies...But How Can This Be Warm?
All the young dudes are knit wits, basically

Yep…we’re talking sides rolled up, ears exposed and possibly even sporting a little peaked top. It makes sense for sailors, who historically wore hats this way in order to allow them to still hear. But today’s teens are rocking AirPods 24-7, and I’m fairly sure nobody is yelling at them to turn starboard anyway.
I asked my 18-year-old son, who sports a couple small knit caps himself, about the appeal, and he simply shrugged and mumbled something about “looking cool.” (At least it covers up hair that needs washing.)
In his defense, the look is definitely a thing. I’ve spotted these tiny little toppers on rappers like Pharrell and Central CEE and across the Fall/Winter 2024 Hermes catwalk. Mall favorite stores are following suit: PacSun is selling a fisherman’s beanie and Urban Outfitters offers a “short roll” knit cap. And hipster men’s clothing etailer Huckeberry is promoting a wool beanie which has, it says, a “short roll design [that] delivers on sleek, low-profile vibe.”
Indeed, micro hats are so popular that Jimmy Fallon and Paul Rudd mocked the style a whole year ago, making me wonder if the “teenie weanie beanie” just might be the new normal.
Armchair parent speculation time: There may be some sort of anthropological use for the micro beanie, as a way for guys to scope each other out as fellow creatives. One Instagram post I saw suggested that the smaller the beanie, the higher the prestige of your job.
It also might be a deliberate “screw you” to the older generation. You know: the kids leaving home in their tiny beanies, rolling their eyes as the Olds who are telling them to wear a proper hat already. In a way, it’s a reverse of the old cliché in which teen girls remove half their outfit once they’re free from the judgey eyes of parents.
And, much like the girl who goes out in February in a mini-skirt and regrets it, I like to picture a teenage boy feeling a mighty wind hitting him upside the head and forcing him to pull down his hat for comfort. You know: Just like Timothée Chalemet.
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