Brad Pitt made waves when he hit the red carpet at last month’s Bullet Train premiere wearing a black linen skirt. The youngins may not have realized it, but it was hardly the first time the 58-year-old Academy Award winner has sparked a conversation about gender norms with his wardrobe: He memorably modeled an array of mini dresses for Rolling Stone in 1999. Those who were shocked clearly hadn’t seen much of him off screen. From the very start, Pitt established that he wasn’t going to dress like your typical movie star—at least for a time: The two decades that followed reliably found the actor in an ordinary tux or suit. Fortunately, Pitt has come to a realization that’s led to his least conventional era yet. “We’re all going to die,” he told Variety of why he wore the aforementioned skirt. “So let’s mess it up.” As we await to see whatever he serves up next, take a look back at his more playful sartorial past.