The Newsboy Cap Is Trending Again, But For This Cali Brand, It’s Always Been Part of Their DNA

The late John F. Kennedy Jr.’s life was propelled back into the public eye earlier this year after the success of the Ryan Murphy FX series, Love Story, which chronicled the businessman and magazine publisher’s romance with Carolyn Bessette.

But Love Story also brought renewed attention to the preppy political scion’s style, with everyone from Timex to Macy’s bringing back iconic pieces inspired by what JFK Jr. wore. While he was known for his relaxed suiting as much as he was for his well-to-do tuxes, Kennedy was also known for his mixing of high and low, often accessorizing his suits with a hat.

It wasn’t just any hat though: People Magazine’s Sexiest Man Alive of 1988 wore backwards baseball caps (repping the New York Yankees), beanies in the winter, and perhaps most memorably, backwards newsboy caps (a.k.a. “flat caps”).

Also known as paperboy caps (or a “paddy cap” in Ireland), the look dates back as far as the 1500s by some accounts, with the wool hat worn by workers to keep the sun and sweat out of their eyes. The newsboy cap was also famously worn by the Peaky Blinders street gang in Birmingham, who inspired the Netflix show of the same name. But it was JFK Jr. who took the look mainstream, pairing a newsboy cap with everything from suits and sweaters, to T-shirts and shorts.

Now, fans of the stylish Kennedy, and menswear fans alike, can get the same look at Brixton.com. The Oceanside, CA-based accessories brand was founded in 2004 — five years after JFK Jr.’s death — but the Brixton story also starts with a newsboy cap. The brand says it was a vintage paperboy cap (that they eventually reworked into their bestselling “Hooligan” flat cap below) that inspired Brixton’s first collection. The brand now sells everything from flannels and beachwear to accessories, but their most iconic pieces continue to be their hats.

Here’s a look at some of the best Brixton hats to buy online right now, including a few that would’ve looked right at home on JFK Jr.’s crown.

Brixton Hooligan Flat Cap

A signature Brixton product, this “Hooligan” flat cap is inspired by a 1920s silhouette, with a flat brim and elevated crown. Wear the hat backwards a la JFK Jr. for a more playful vibe or wear it flat side forward for a more traditional look. We like the herringbone pattern, which has the look of tweed but is made with a lighter and more breathable polyester. Five colors are available. Choose from sizes XS to XL.

Brixton Brood Newsboy Cap

This newsboy cap features a shorter brim and a fuller, rounded crown. The brown herringbone pattern adds to the vintage appeal, while a metal crest pin on the side adds a subtle stylish detail. Multiple colors are available (including a solid black) in sizes XS to XL.

Brixton Fiddler Fisherman Cap

This fisherman cap is an iconic silhouette that was once associated with sailors and the high seas, but it works today as a retro-tinged accessory for both preppy and nautical style. The hat features a flat top and slightly-curved brim with corded detailing and a metal pin on the front. Brixton says this model was inspired by a style that originated from the 1950s. Choose from sizes XS to large.

Brixton Crest Snapback

And if a newsboy cap isn’t for you, do like JFK Jr. and pick up a classic baseball cap. We recommend this one from Brixton, which features a classic structured fit, five-panel design, and adjustable snapback closure. The brim can be flexed straight or curved depending on your style. Brixton says the visor is made from recycled fishing nets, while the main hat is made with a moisture-wicking material to keep you cool.

Brixton has multiple baseball cap styles available on its website though we’re partial to this wear-with-anything black and white version with the Brixton logo crest on the front.