It’s baseball hat season, baby. And even though wearing one might seem simple, there are a few considerations to keep in mind. If you want to nail the shape, the style, and the vibe, this definitive guide will show you how to do it right all summer long. —Jonathan Evans, style director
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From what to wear to where to wear it, here’s what you need to know.
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It’s baseball-cap season. That’s true in the literal sense; MLB is currently going strong. But it’s also a philosophical declaration. Because even if the idea of hitting a small white orb with a piece of wood and then running around a field were to disappear from the popular consciousness, it’d still be baseball-cap season. Because with Memorial Day rolling in, we’re just about to hit the unofficial start of summer. The sun will shine, the temperatures will soar, and headwear that keeps the glare out of your eyes and the sweat off your brow will become more essential than ever.
Of course, the prevalence of the baseball cap during the warmer months raises some questions. Should I be wearing one? What kind? Where? These are all valid queries, and the short answers, if you’re feeling impatient, are: sure, it depends, and it also depends. But you’re not here for the short version. You’re here to examine the nuances of the baseball cap in 2026 and figure out what works for you and when.
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Tucker Pillsbury has recently taken up old school fishing. “I'm gonna go to a fishing store after I speak to you because I want to get a new fishing pole,” the singer-songwriter, who is better known to his legions of fans as Role Model, tells me over a video call from his Los Angeles home. “It's my new hobby. I grew up fishing and my mom recently visited me and realized I don’t have any hobbies, so suggested fishing again.”
Role Model, who is currently working on a “vibey and fun” new album, hails from the scenic shores of Cape Elizabeth, Maine, which he left to study film at Point Park University in Pittsburgh, Pennsylvania. It was in 2018 that his career as a musician took off, when the late Mac Miller caught wind of one of his songs “Stolen Car,” a ballad about addiction. After discovering Role Model's early homemade tracks, Miller reached out, took him to Los Angeles to collaborate, and became a mentor to him in the music industry. The rest, as they say, is a colorful history of Coachella sets and TikTok viral hits—a trajectory that meant the 29-year old artist never went back to Maine.
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I guess I should take the next couple years off. Way back in Trump’s first term, Ol’ Tom Massie summed up the modern Republican party far beyond my own simple powers to do so. And he can go off into oblivion knowing that it took nearly $20 million to beat him because he sought justice for the victims of celebrity sex maniacs. That’s something, I suppose. And—for me, anyway—the real ray of light in Tuesday’s elections came from Alabama, where Senator Tommy Tuberville won the Republican nomination for governor. As much as I like Doug Jones and wish he would become governor, Tuberville is favored. At least his abject stupidity won’t afflict us on a national basis anymore. It will become solely a problem for Alabama. They can have him.
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