During the “Golden Age” of cinema, there were a handful of actors who—through a combination of on-screen performance and real life antics—were the definitive face of Hollywood. Buster Keaton, Clark Gable, Marlon Brando and many others shaped the mold for the modern A-list leading man. If any one today can measure up to these greats, it’s none other than Brad Pitt. Easily one of the most recognizable men in film today, no one else juggles blockbusters, critical darlings, producing and even directing quite like Pitt. With a filmography spanning more than 80 pictures, filled with as many summer blockbusters as cult classics, Pitt’s versatility, work ethic (and jawline) is unmatched in Hollywood today.

While his career began firmly in hearthrob territory, through innumerable performances Pitt proved that he not only had the acting chops, but commitment and swagger to match those luscious locks. Although his persona today is more akin to “sober dad”—with the off-duty style to match—on-screen Pitt ranges from grizzled hunk to contemplative octogenarian, looking immaculate all the while. Granted, when you’re that handsome, it’s not too difficult.

With the release of his latest film, Once Upon a Time In Hollywood—set precisely during the Golden Age of Hollywood—we are breaking down Pitt’s most memorable costume choices. While we already ranked co-star Leonardo DiCaprio’s various on-screen get-ups, what separates Pitt from the crowd is a universal charm, wit and amenability that elevate every scene he’s in (and the clothes he wears within them). While some choices are obvious, others are more focused on the films sheer style—rather than the film itself, or Pitt’s performance for that matter. Let’s be frank, Pitt isn’t just an actor, he’s a movie star. He’s bound to have some duds.

That said, from Tyler Durden’s unbridled machismo to Rusty Ryan’s Vegas-meets-Miami sartorial savvy, Pitt’s characters never fail to leave an impression. As long as he continues to act (which could very well be decades), remains handsome, and looks this good in essentially anything, he will continue to do the same.

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