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.
A 25-year-old Pitt was at the very start of his career when he donned a pale pink bandanna for this unconventional handout photo.
He was part nerd, part rocker when he attended the Los Angeles premiere of Red Heat wearing a leather motorcycle jacket and glasses.
Ripped jeans and a graphic tee for a day on the slopes? The ones that Pitt hit with his then girlfriend Shalane McCall were actually constructed for a March for the Dimes benefit in sunny Los Angeles.
And so begins Pitt’s devotion to couples style. He matched his onetime fiancée Jill Schoelen in a wide-brimmed black hat at the launch of the Mondrian Models & Photographers Club.
He would go on to make jeans his signature ensemble for premieres like that of Eddie and the Cruisers II: Eddie Lives!.
In fact, Pitt—seen here with E. G. Daily at her album listening party—could reliably be found in light-wash jeans in the late ‘80s.
He matched them with tinted blue sunglasses at the Los Angeles premiere of Thelma & Louise.
Imagine Pitt looking so casual at the My Private Idaho premiere if the film were released today.
Formalwear, but make it Brad—who was then dating Juliette Lewis—in his early thirties.
To match the hippie vibes of his long hair, Pitt wore a colorful paisley button-down to the Los Angeles premiere of True Romance.
By the time he attended the next year’s VHI Honors Awards, his look was much more Kurt Cobain. (Who just so happened to also be a light wash denim lover unafraid to wear a dress.)
Seriously: ‘90s era Brad—seen here with Jitka Poheldek at the Legends of the Fall premiere—was made to star in a biopic of the Nirvana frontman. (We’d agree with Courtney Love that Pitt isn’t right for the role in the present day—though would probably use softer phrasing than “Kurt had more presence and more beauty than Brad” to explain why.)
Ah, the Gwyneth Paltrow era. Whereas Pitt uncharacteristically wore corduroys when they stepped out in New York City, Paltrow channeled old Brad in a leather jacket and light wash jeans. (Made all the better by the ultimate accessory: a copy of this very magazine.)
Between the previous look and the above sweater vest he wore to the premiere of The Pallbearer, you may think that Pitt aired on the preppier side over the course of their three-year relationship. Allow the two slides that follow to prove otherwise.
The hair stylist Chris McMillan was (accidentally, per Paltrow) responsible for their matching haircuts at the premiere of The Devil’s Own. As for their matching black ensembles? Perhaps the pair was in mourning for the relationship that would end later that year.
Whatever the reason, Pitt seems to have had a predilection for black that spring. For the record, Brad, while you’re at it with experimenting, we’d love to see you give goth another go.
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