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.