Looking through the archives (and the excellent @nightopenings Instagram account), a few serial hat wearers emerge. In the ’90s, Chevy Chase showed up in everything from a prop police hat from a Dan Aykroyd movie to a statusy souvenir cap from a restaurant in St. Barts. The legendary Buck Henry was loyal to the look, too. Christian Slater—a pro at pairing a good hat with a double-breasted blazer—had a deep bench of sporty headwear, including one touting a Mike Tyson fight at The Mirage. And, of course, there was the era’s megastar, Bruce Willis, a man who pulled off caps with bomber jackets and loafers just as easily as popped polos and blue jeans.
Looking through these images, a theme emerges: The apex of the form was the promotional hat—a kind of self-marketing so earnest and obvious it now feels quaint. Both Willis and Samuel L. Jackson showed up in swagged-out Die Hard promotional hats. (In 1993, Jackson did the same for Menace II Society; that whole decade and beyond, Willis did it for nearly everything from Armageddon to The Sixth Sense.) Danny DeVito wore a Gattaca cap; Hayden Christensen an “Episode III” hat. And then there was Spike Lee, the undisputed monarch of the promo cap, whose relationship with New Era helped reshape the baseball cap entirely. Malcolm X, Mo’ Better Blues, and Girl 6—each got its own signature lid.
Today, the idea of wearing a baseball cap to an A-list premiere feels like a lost art—and given that hyped-up Marty Supreme jackets are now going for four figures on Grailed, the simplicity of a promotional cap feels especially potent. There have been recent flashes: Jonathan Bailey channeling a baseball-capped ’90s-era Spielberg at the Jurassic World Rebirth premiere (a finely executed, if somewhat too on-the-nose, nod to the movie he was promoting), or the late Rob Reiner in a matching Spinal Tap cap and T-shirt last fall. Nevertheless, more modern torchbearers have emerged, including the deeply underrated dresser Lionel Boyce, who has donned covetable Ebbets Field caps on multiple occasions, and Bad Bunny, who regularly pairs brimmed hats (worn both forwards and backwards) with his suits.
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