‘Once Upon a Time in Hollywood’ Style: Are You Pitt or DiCaprio?

The Hollywood of the ’60s was a fairy tale.  Some of the greatest cinematic works were produced in this era—from Butch Cassidy and the Sundance Kid to To Kill a Mockingbird to Lawrence of Arabia—with stars that epitomized Hollywood glamour. 

It’s therefore fitting that the leading men in Once Upon a Time in Hollywood, Quentin Tarantino’s latest film about two men making their way around the hippy Hollywood scene of the ’60s, are two of the most recognizable faces in the industry today. Leonardo DiCaprio and Brad Pitt are veritable icons with decades-long careers. And while a Hollywood movie filled with tributes to Hollywood may seem meta or even self-serving, in the hands of Quentin Tarantino it’s a spectacle, managing to showcase both the enchantment and underlying darkness of 1969 Los Angeles. 

Set exactly 50 years ago, the film features ’60s-inspired costumes designed by Arianne Phillips that are as sentimental as Tarantino’s homages to classic cinema. The story follows aging actor Rick Dalton (DiCaprio) and his stunt double Cliff Booth (Pitt) as they attempt to navigate the film industry. The two men boast bold looks, but each has a distinctive style. 

Is your personal style more Pitt or DiCaprio? Take a look at these ensembles and affordable ways to replicate the fits below. 

While not every ’60s man fully relished the age of flower power, hippie and bohemian influences greatly impacted the decade’s fashion trends. Rigid, formulaic fashion gave way to looser, more colorful pieces. Pitt and DiCaprio’s fits above demonstrate the funky fashion choices that the ’60s allowed, like DiCaprio’s bold Chinese dragon–print loungewear. Hawaiian shirts, like Pitt’s, have made a true resurgence in pop culture this summer. Pick a print and wear it proudly—the men of the ’60s would applaud you.

While perhaps not the most apropos shoes for the maneuver DiCaprio is attempting above, heeled boots gave men a lift in the ’60s. Platform boots were all the rage for men striving for a few extra inches. Suede and leather were just as popular in footwear as they were in outerwear, but casual shoes could be more relaxed. Like Pitt, many men opted for more easygoing moccasins or chukka boots. 

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