Boots Riley’s gloriously big hats have become an essential part of the press run for his latest flick I Love Boosters, out Friday. Profiles of the Oakland rapper-turned-filmmaker in The New Yorker, the Los Angeles Times, GQ (naturally), and even Mother Jones (good for them!), all published in the past few weeks, all dwell on the hat in some detail.
It makes sense: Riley’s hats are nothing if not noticable. Lately, he’s been rocking a turquoise one almost exclusively, whether at the Oakland premiere of Boosters at the Grand Lake Theatre, the screening of Sorry to Bother You at the Alamo Drafthouse New Mission a day later, or in his charming Criterion Closet appearance.
The hats are from a London brand called Uptown Yardie, a British milliner inspired by founder Rohan Clarke’s Jamaican heritage. Riley is partial to the “Garvey Crown” hat, which has two dimples on its crown and retails for about $470.
He’s certainly not the only celeb to wear Uptown Yardie’s hats: They’ve been spotted on Erykah Badu and Beyoncé’s publicist Yvette Noel-Schure. But in recent years, it has become a defining part of Riley’s look, so much so that at least one piece of promotional material for Boosters features an illustration of the hat. It is the piece of fashion iconography that you associate with him, the way that you connect Martin Scorsese with his large, horn-rimmed glasses, or Spike Lee in his eye-catching sneakers, or John Waters and that pencil-thin ‘stache.
In his New Yorker profile, Riley mentions that he started wearing the hats for a practical reason: His hairline is receding. He also wondered aloud if he should stop wearing them in that interview; heavy is the head that wears the Uptown Yardie hat.
Riley appears to own the hat in just about every shade: In addition to the turquoise hat he’s worn a lot lately, he’s been photographed with the hat in black, burnt orange, and grayish-pink versions in the past couple of months.
To celebrate the release of a movie from one of the Bay Area’s most celebrated directors, we made a very incomplete timeline of Riley’s love affair with Uptown Yardie hats in the lead-up to Boosters.
January 2023
Boots was first spotted publicly wearing an orange-red version of the Garvey Crown during the 2023 Sundance Film Festival. He paired it with a fur coat, and joked to Vulture that he could hide food in this hat, a la Paddington.
“This is something a teddy bear would wear,” he told Vulture.
March 2023
In a recorded SXSW panel after debuting the 2023 Amazon Prime series I’m a Virgo, Riley can be seen wearing one. This one is in a lovely shade of kelly green. The hat, incredibly, also covers most of Walton Goggins’ body over the course of the Q&A.
November 2023
He shouted out the brand in an X post, the first time he’d mentioned Uptown Yardie. After he took part in a Variety panel, he fielded a question from a fan about his hats — and has continued to do so repeatedly online.
December 2023
A month later, he declared his allegiance yet again to Uptown Yardie’s hats. One eagle-eyed local fan spotted him at the New Parkway in Oakland during a screening of Boy and the Heron. The user @endeus07 said he was wearing the same hat he wore at Sundance, attaching an image of him with that Paddington-esque ‘fit.
Nope. I'm a man of many hats. This was the one. Close though. (Pic by Richard Maltz) https://t.co/iiDn4v0CqK pic.twitter.com/TcawH33q7A
— Boots Riley (@BootsRiley) December 31, 2023
Riley corrected him; he was, in fact, wearing the same red hat from the month prior: “I'm a man of many hats.”
May 2024
Again, even on a Zoom Q&A for the awards site Gold Derby, he’s wearing an Uptown Yardie Garvey Crown in a deep-red hue.
August 2024
There’s that red hat again! He wore it in a talk he did for Oakland nonprofit YouthBeat. He’s sticking to the colors he loves, and there may be a story behind why he gravitates toward certain colors during certain phases of his life. Only he really knows how he chooses his hat for the day.
January 2025
Riley was largely out of the spotlight after the press run for I’m A Virgo, presumably while the director was hard at work on Boosters. The one Uptown Yardie hat that we could find is in this Instagram post with him and Tune-Yards, the Oakland group and longtime Riley soundtrack collaborators. This hat is new, though: It looks closer to the Kingston Crown, which is made with a woven fabric.
January 2026
He’s really not wearing hats! Even at the SFFILM Awards Night in December 2025, he wasn’t wearing a hat. But, fittingly, at Sundance, where Riley was first spotted with them, he was wearing a hat in a picture with Sundance celeb selfie-taker Stuart Graves. It might even be the same red-orange that he wore at Sundance 2023, when his infatuation with Uptown Yardie hats began.
