The Newsboy Cap Is Hot, Actually

If you see me out running errands, odds are I’m wearing a baseball cap. I have one for nearly every mood: the Yankees x MoMA one every New Yorker owns, a My Chemical Romance concert merch cap, a maroon one from a trendy café in Paris, a green one with the title of one of my favorite movies stitched in the front in jagged white letters. They give a little personality to my otherwise simple rotation of black baby tees, baggy jeans, and ballerina flats, and, as a woman of the large-forehead experience, they keep me looking proportional and cute, especially when I don’t have bangs. But before the baseball cap, there was another hat in heavy rotation, a cap I’m eager to bring back this fall: the newsboy.

Technically, it was a Brixton Fiddler Fisherman cap, but it shared many of the same qualities as a newsboy — a slightly rounded body, a short, stiff brim, satin lining. I wore it with my shearling leather jacket and ankle boots, with braids and a black turtleneck like that one photo of Kate Moss in 1990. I wore it with band t-shirts and ultra mini skirts, with oversized wool sweaters and my ex-situationship’s vintage Pendleton jacket. In 2018, it didn’t strike me as a particularly risky choice. When I plopped it on my head, I thought I was conjuring the same spirit as the ’60s and ’70s icons I’d been obsessed with since my teens.

And they really did wear it best. As Vogue pointed out at the height of the revival in 2016, “virtually every one of your favorite style icons from the ’60s and ’70s tried one on for size.” From Jean Shrimpton, who “elevated the formerly pauper piece to glam new heights,” to Jane Birkin who “made a very strong case for trading a career on film for one along the pier.” The newsboy cap was a shapeshifter, toggling between gamine, sexy, counter-cultural, and downtown-cool depending on the wearer.

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So it never occurred to me in 2018 that the hat would read as less French ingénue and more Glee side character, or worse, Mumford & Sons. When I bought it, I was thinking about Dsquared2 Spring 2013, which I must’ve watched at least a dozen times on the Fashion Channel YouTube (I remember Women’s Wear Daily described the show as being “very S&M Barbie,” with its itty-bitty micro shorts, stacks of gold chains and pearls, and leather newsboy caps), using it as proof that the newsboy cap was, indeed, hot. I was thinking of Anna Karina. I was thinking of Peter Linbergh’s famous 1991 photograph, The Wild Ones. But my aforementioned ex-situationship, a creative director who lived in Soho, thought that, much like my aviator Ray-Bans, the cap was definitely, totally, 100% out.

I hate to say it, but he was right. By 2019, the hat was deemed overexposed, unsexy, and as The Cut put it, “the black turtleneck of accessories, giving the wearer a false sense of intellectualism.”

Ouch.

But here’s the thing about fashion purgatory: no one stays there forever. Chanel’s pre-fall show in late 2024 featured candy-colored tweed newsboy caps, and Anne Hathaway, who wore it as Andy Sachs in The Devil Wears Prada, has been wearing hers with silver boots and wide-leg jeans. Kendall Jenner was spotted in one earlier this year (with her fresh bob and straight leg jeans, I couldn’t help but say out loud, “Hey, twin!”), and Addison Rae can’t stop wearing hers.

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Even Vogue has declared that the newsboy is back, but not everyone is convinced.

“I have a blue and green plaid one somewhere I’ve been trying to get rid of for like, three years now,” said Nicole Barley, a 25-year-old creative strategist. “I remember watching High School Musical when I was younger and seeing that hat and [thinking], ‘Now why would they do that to them?’”

Good question. Why would the costume department do that to characters who were supposed to be in high school? But then again, is it worth questioning any of the choices Disney’s costume department made in the 2000s?

I told Barley I was thinking about reviving it. “You gotta wear it backwards,” she said, and sent me a few cute images as inspiration. “Even that is on thin ice with me.”

I could understand her perspective. Even a backwards baseball cap can be considered an interesting choice (and it’s a choice I’m always happy to make).

But the newsboy cap — specifically in its 2000s iteration — has its supporters. “I wore one as a girl because Britney was in Rolling Stone, photographed by Peggy Sirota wearing one. And I thought, all I need is one of those and a matching crop top and I, too, can be fabulous,” said 30-year-old publicist Naomi Leigh.

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Kohlea, a 28-year-old pop culture historian teaching English in Korea, agrees. She’s the proud owner of a vintage Playboy cap she thrifted in Japan. “[Newsboy caps] mostly remind me of 2000s fashion more than anything else,” she said. “[They’re] becoming popular in Korea and Japan again because…of 2000s anime characters and dress up games.”

Perhaps this is the secret to a worldwide newsboy cap revival — if we treat it like other controversial 2000s trends (ultra low rise jeans, hot pink Juicy Couture tracksuits, capris), it suddenly feels less stomp-clap and suspenders and mason jars and more like a playful, IFKYK throwback. Think Tyla in her burnt orange newsboy cap at the Kids’ Choice Awards this year, looking like she stepped right out of a Y2K music video.

So if you see me out running errands this fall, odds are I’ll still be wearing a baseball cap. But don’t be surprised if I’m back in a newsboy. There’s one waiting for me on eBay, and I’m not afraid to click “Buy It Now.”