Once Upon a Timeline: The Endless Style of Brad Pitt Over the Past 30 Years
Regardless of gender, it’s impossibly difficult to be stylishly sexy all the time. Except in the case the style of Brad Pitt. The 56-year-old actor seems to only get more attractive with age, something that’s not easy to do. The Benjamin Buttoning of Brad Pitt doesn’t just have to do with his super perfect body, boyish grin, and chiseled abs, but his evolving sense of style, which we’ve had the pleasure of peeping as he’s matured into one of the finest actors in Hollywood. Is this the work of brilliant stylists, the fact that he’s a method actor, or is he simply influenced by the different relationships he leaps into and out of? One thing’s certain: he’s never looked better. Keep reading to experience the endless style of Brad Pitt over the last 30 years.
Photo: Vittorio Zunino Celotto / Staff (Getty Images)
Brad Pitt ranked: 12 Favorite Movie Roles (Before ‘Once Upon a Time in Hollywood’)
'Thelma and Louise' (1991)
All Brad Pitt needed to become a cultural icon was a blow-dryer, a cowboy hat, and to steal any chance Thelma and Louise had to escape.
Ultra grungy psychopath Brad Pitt with cameos from the real star of the show: his abs.
'Interview With a Vampire' (1994)
Homoerotic vampire in a relationship/non-relationship with both Antonio Banderas and Tom Cruise.
'Legends of the Fall' (1995)
Turn of the century style that has Pitt riding horses and his dead brother's fiancée.
Pitt wears the perfect outfit to find out "What's in the box?"
'Meet Joe Black' (1998)
A film so sappy, it features death coming to Earth as a pretty boy version of Brad Pitt who also loves peanut butter.
'Fight Club' (1999)
The forgotten first rule of Fight Club is to take off that thrift store shirt and show off those abs.
Although you can't understand a word he says, his abs knock us out better than Pitt's world-class punches.
'Friends' Cameo (2001)
On this Thanksgiving episode of Friends, Brad Pitt shines as the former fat kid tortured by his then-wife, Rachel Green, portrayed by Jennifer Aniston.
'Oceans 12' (2004)
No abs, but a buzz cut that isn't inspired by Space Monkeys.
'Mr. and Mrs. Smith' (2005)
The movie that ruined Jennifer Aniston's life.
'Inglorious Basterds' (2009)
The start of the ultra puffy, he's-probably-drinking-too-much era.
'By the Sea' (2015)
The movie that let the world know Brangelina would not last.
'Once Upon a Time in Hollywood' (2019)
And the film that reminded us that Pitt should only be allowed in films where he takes off a shirt that is obviously from a thrift store.
Golden Globe Awards (2020)
At 56, Brad Pitt's still better looking than anyone you've ever dated, regardless of gender.
Brad Pitt alert: Brad Knots His Shirt in GQ Shoot, Reminds Everyone They’re Not Brad
Which time period in Brad Pitt’s evolution of style is your favorite? Sound off when Brad was peak Brad Pitt stylistically in the comments!