A Visual History of Leonardo DiCaprio and His Endless Hat Collection

When Jeff Bezos and Lauren Sánchez tied the knot earlier this summer, an A-list crowd of wedding guests gathered in Venice for the splashy affair. With paparazzi lingering at every corner, most attendees dressed to be seen (see: the entire Kardashian family, Oprah Winfrey, and Sydney Sweeney) though other stars chose to fly more under-the-radar. Take Leonardo DiCaprio, who spent the entire weekend concealing his face underneath a sleek black baseball cap—an unsuccessfully-incognito move. “Leo DiCaprio thinking a hat pulled low and he wouldn’t get recognized,” wrote one Threads user.

The face-concealing cap has become DiCaprio’s signature accessory. These days, you rarely catch the Oscar-winning star out on the streets without one. Whether he is vacationing in Ibiza with his model girlfriend Vittoria Ceretti, or attending Paris Fashion Week in the front row, wearing a low-slung hat has become DiCaprio’s personal form of armor at all times—a strategic wardrobe staple to fend off any eye-contact with fans seeking autographs or selfies. When duty calls, movie star Leo will hit a red carpet premiere sans chapeau—but if that humble cap is on during a day off, it proclaims: Leave me alone!

A quick look back on DiCaprio’s off-duty style, however, and you will find that the actor has worn the utilitarian cap for years—long before sneaky iPhone pics were even a thing. When he first burst onto the scene as a Hollywood heartthrob in the ’90s, you could often find DiCaprio wearing caps from his favorite sports teams. He has worn team merch from the Lakers, Boston Red Sox, Florida State Seminoles, Golden State Warriors, and countless others. (Go. . . sports.)

A camera-shy DiCaprio back in 1999

Photo: Getty Images

As his star has steadily continued to rise, DiCaprio’s beloved caps took on a new meaning. What likely stemmed from a love of sports and casual dress, has since evolved into the star using hats as a shield from prying eyes. His eye-covering hats are so synonymous with his style, that there are now TikTok videos dedicated to making your very own paparazzi-proof Di-CAP-rio (get it?). People have also spoofed his hats by wearing styles with extra-extra-long brims.

You can make fun of his devotion to hiding under hats all you want, but remember that privacy is a luxury—and a $30 cap is an effectively cheap way for DiCaprio to get it on the daily. Can you blame him? Other stars have their signature accessories: Diane Keaton her brimmed hats, J.Lo her Birkin bags. But there is something charmingly low-fi about the endless array of DiCaprio caps. We wonder how many are in his wardrobe. At this point, he must have a different one for every day of the year—or the next five.

Below, see more images from DiCaprio’s life in hats.