The man, the myth, the legend—there’s few in Hollywood (or on planet Earth) like Leonardo DiCaprio. From teen heartthrob to Oscar-winning actor, DiCaprio is a stalwart of today’s celebrity culture. It’s hardly his cinematic chops that have kept him in the spotlight though; DiCaprio’s fashion choices both on and off the camera have made him a men’s style icon (to say nothing of his notorious antics dating a running series of under-25 fashion models). Examining DiCaprio’s entire library of looks though: off screen, his casual style keeps him incognito—there’s no question that his on-screen looks are his most memorable.

If DiCaprio is praised for his ability to transcend film genres to deliver a great performance, then his ability to pull off a myriad of styles—from reckless Shakespearan romantic to Wall Street power suit—is all a part of his string of successes.

As his second film with Quentin Tarantino, “Once Upon a Time in Hollywood” hits theaters later this week, we’re diving deep on DiCaprio’s most stylish silver screen outfits. Given DiCaprio’s stacked filmography, we’ve singled out a few classics, as well as spotlit a few unconventional choices; it’s only fitting for someone with such one-of-a-kind unconventional talent.

From the flamboyant fits of Romeo Montague to the ostentatious ’80s wardrobe of Jordan Belfort, it’s clear that DiCaprio’s films (and the style found within) stands a cut above.

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