Why Do Guys Wear Beanies on the Tops of Their Heads Now?

In New York, where I live, it’s almost like a plague out of a horror movie. Uptown. Downtown. Brooklyn. Queens, presumably. The young men all have it, drawling dead-eyed through Tinder dates as if they don’t even know it’s there. “It” is not seasonal affective disorder, nor a near-fatal addiction to Sweetgreen, though we presumably all have those, too. “It” is something perhaps even scarier: a beanie, crisply cuffed, perched jauntily right on the top of the head (and leaving the ears exposed to the elements).

I’m one of the afflicted. I’d always been a back-of-the-head man come winter, privileging warmth—and a certain late-’90s emo-band vibe—when it came time to cover my head. Last winter, though, as if I’d been invaded by a body-snatcher, I found myself striding out of my apartment with a hat that left my ears dangling, Dumbo-like, in the cold winter breeze.

How did this happen? When did the beanie transition from functional cold-weather accessory to all-weather fit-topper? Who was behind the shift? And what might it say about the state of men’s style?

I put on my dumb, tiny hat and went looking for answers.

Warm knit caps have been around for centuries; as happens so often in the history of clothing, the military version of the garment was the one that springboarded into pop culture. That was the “watch cap”—so named because Navy sailors wore them to keep warm while keeping watch overnight. It quickly migrated into civilian fashion: Archival photos of Steve McQueen in a watch cap suggest that the actor appears to have never kept his ears warm, Jack Nicholson’s hat in One Flew Over the Cuckoo’s Nest barely grazed the tops of his, and Marvin Gaye inspired a thousand ill-fated red caps. Seventies and ’80s beanies were Technicolor nightmares with pom-poms, and in the ’90s the early extreme-sports boom led to hats that were big, baggy, and reservoir-tipped.

But to my mind, the beanie really came of age as a fashion accessory in the late aughts. In Los Angeles, where I grew up, the beanie is essentially useless 11 months of the year. And yet, over that period, it flourished, particularly as part of an outfit I’ll call the My Friend’s a Promoter Special. You’ve seen it before: heavily distressed skinny jeans; pointy suede Chelsea boots; a very long, very thin T-shirt with a distressingly wide neck opening; and a beanie placed artfully over the crown of the head, covering the ears but almost none of the forehead. Here, the beanie addressed different needs for different guys: man-bun storage, bald-spot coverage, jacket-warmth replacement. As menswear fanatics ditched suits and spread collars for Kanye-approved layering techniques, the beanie rose. And then, just as quickly, it was supplanted. As the fashion world became obsessed with the sport, it began to ape the skate world’s model beanie—and as the beanie became a decorative accessory, not just a functional one, guys had to find a way to wear them inside and in warm weather without overheating. Hence the top-of-the-head look.

Still, though, this felt flimsy. So I went to an expert.

Tinyhat_Skatelife is an Instagram account devoted to the semiology of the top-of-head beanie. Taken in full, the page sketches a comprehensive image of the tiny hatsman: His style, more advanced than basic, borrows from the world of skateboarding; his manners are horrendous. In an e-mail, the account’s proprietor helped fill out the picture, explaining that the top-of-head beanie can say a lot about a guy.

“Tiny hats span so many different subcultures (besides skaters), so it’s hard to specifically say how this person may act,” Tinyhat wrote. “But to sum it up real quick, I’d say someone who is wearing a tiny hat is either one or all of these things listed below (these are all assumptions, obviously):

• Skater – unemployed
• Works at a coffee shop – in a band or writing a novel
• Works at a gallery – fake deep/fake woke
• Hypebeast – has rolled up their Supreme beanie so it barely touches their ears, you can still see the logo though.
• Or like whatever you bought a hat at urban outfitters and wanna fit in so you rolled it up a bit and thought you looked good.”

After being discharged from my local hospital’s burn unit, I asked Tinyhat about the differences between a tiny beanie man and a saggy hat boy. She was succinct, and crushing: “Easy, the guy with the tiny hat is the guy you want. Unfortunately he doesn’t text you back and when he sees you at your local bar he walks the other way. The guy with bigger, saggier beanie is the one who won’t stop texting you, tries to take you on dates, asked you to see mid 90’s with them. But ya know there is something you’re just not attracted to about him.”

If the top-of-head beanie renders a guy attractive, I was learning, it’s because the hat signals a level of vulnerability. (That the tiny-hat wearer is fundamentally incapable of empathy lends the dynamic a certain dramatic irony.) Notable small-hat wearers, per Tinyhat, include Bill Murray (“every skater / artsy boy is like obsessed with Bill Murray so it’s no wonder one of the tiny hat icons is from a Wes Anderson film”), Tyler, the Creator, and singer Mac DeMarco (“always wearing a tiny hat, skaters think they are deep for listening to him also”).

Slowly, DeMarco’s wistful “Salad Days” twinkling in my ears, I began to formulate a theory.

Maybe it’s optimistic to think that, as millennial men gave themselves permission to engage in fashion as a hobby over the past five or ten years, they got in touch with sides of themselves that had previously been closed down. Or, to put it into structural terms, I don’t think it’s a coincidence that, as the caricature of the millennial shifted from an avocado-obsessed profligate to the victim of a series of world-rending economic forces, the beanie migrated from the back of the head to the top. If the saggy beanie was representative of pre-housing-crash optimism, covering up insecurities while taking out a second mortgage on its luxury condo, the top-of-head beanie suggests a coming-to-terms with the idea that anyone under 40 is on the short end of a long-tail economic crisis.

That, or we all just remembered what Steve McQueen, Mac DeMarco, Tyler, the Creator, and Bill Murray have in common: They all wear tiny hats, and they all look really fucking cool.