Brad Pitt’s dramatic style evolution: from the late ‘80s and ‘90s to ‘00s

Brad Pitt in the late ‘80s was into bold muscle tanks, light wash jeans, and high-top Adidas sneakers. Aside from being genetically blessed with good looks, at the time, his cool-dude attitude couldn’t be any more convincing – especially when wearing dark sunglasses and a light pink bandana.

That same year, the young actor also showed his liking for black and white, which is something he maintains throughout his style evolution. Here, he rocks a classic leather bomber jacket, roomy trousers and a basic white T-shirt.

Between the buttoned vest, the stylish Fedora hat, cross-shaped necklaces and steel-toe boots, this look couldn’t be more ‘80s, wouldn’t you agree?

Denim on denim topped with an oversized sports coat was Brad’s style of choice for a red carpet event in 1991. The Babel actor wore this casual-yet-elevated look to the Thelma & Louise movie premiere in Los Angeles. Brad accessorized with a pair of round tinted sunglasses and suede boots – another closet staple of his.

Once again, the Troy actor rocks a bandana. This time he styled it with a pair of light blue jeans and a loose button-up shirt featuring an extreme V-neck and rolled up sleeves. This outfit is the epitome of classic American laid-back style in the early ‘90s thanks to denim and the bandana detail.

The Hollywood star continued experimenting with his looks. During the True Romance era, Brad continued his affinity for button-up shirts, rolled sleeves and V-necklines. He also welcomed long fairytale prince-like hair, which paired well with that handsome face of his.

That same year, the Fight Club actor continued his grungey style phase, which is synonymous with the ‘90s. This is the longest we’ve ever seen his hair, but of course, he pulls it off because he‘s Brad Pitt after all. For this red carpet event, the actor took his jeans and suede boots to a higher level of relaxed with a loose grey sweater.

No, that’s not Kurt Cobain! With bleach blonde shoulder-length hair, Brad could’ve easily passed as the Nirvana frontman. Although he radically changed his hairstyle, the movie star kept some of his wardrobe staples when he appeared at VH1 Honors wearing blue jeans and his trusty pair of suede boots. He paired them with a striped vest and a basic long sleeve shirt.

While promoting his film Legends of the Fall, Brad continued his romance with light blue jeans, but this time he went for lace-up boots. This layered outfit continues to be on the easygoing side of syle, but he added an edgy touch with a pair of dark sunglasses.

For the Pallbearer premiere, the producer appeared with his girlfriend at the time, fellow actress Gwyneth Paltrow. Brad’s sweater vest stole the show, and the pair slightly matched with slim rounded sunglasses and light-colored clothing.

But then their level of matching went to an all-time high when they twinned with the same hairstyle and went to The Devil’s Own premiere wearing head-to-toe black – minus Gywneth’s printed red top peeking from under.

What’s cooler than spiked hair and red-tinted sunglasses? Pairing them with a sharp suit. That’s just what Brad did when he showed up to the John Huston Awards honoring Tom Cruise.

The Fight Club actor suited up for the premiere of his film in a three-piece navy suit and a light pink shirt. He was accompanied with his girlfriend at the time, Jennifer Aniston.

It doesn’t get more ‘90s than this shot of Brad and Jen– everything from the baggy pants, the casual tops, the flip flops and small, wasp-like sunglasses.

It’s the year 2000 and the then-couple dressed up, matching in head-to-toe black for the American Film Institute honoring Harrison Ford. Unlike today’s affinity with tailored and slim-fit trousers, Brad’s early 2000s suit continued featuring baggy pants.

By now, we can testify Brad was an avid user of baggy cargo pants. Here, he teamed them with a light green top and added some edge with a button leather jacket.

You may recall, guys at the club started dressing like this circa 2003. Brad’s jeans started to get less baggy, meanwhile, button-up, collared shirts featuring geometric patterns were considered to be popular.

A tailored suit on Brad is possibly one of our favorite looks on the Meet Joe Black star.

Brad attended the 2008 Independent Spirit Awards with his girlfriend at the time, Angelina Jolie. The Inglourious Basterds actor slipped into some dapper fits, including a pair of plaid grey pants, a crisp white shirt and a classy suede jacket with tan-colored boots to match. The look is a perfect mix of cool and sophisitcated.

A smart cream-colored suit gets redefined when you add a scarf, aviator sunglasses, and two-toned shoes à la Brad Pitt.

While at a football game with his oldest son, Maddox, Brad showed his hipster-ish, off-duty side with a loose beanie, a hoodie, and a zip-up leather jacket. His scruffy beard adds to the laid-back attitude.

Despite his gift to pull off anything, the businessman is no stranger to a classic black suit and white shirt combo.

During his Fury era, the Hollywood star went mad for plaid with a checkered shirt and blazer. Brad’s dapper style remains easy-going yet elevated with the merge of jeans and a tie.

His suede boots are back, but this time you’ll notice they’re paired with dark, tapered jeans and a fitted button-up shirt rather than loose-fitting clothing circa 1999. The Seven actor showed more of his high fashion sense with a leather bag, lightly-tinted sunglasses and a fedora hat.

While his accessories remained the same, the Golden Globes award-winner took a monochrome approach in dark blue jeans and a matching shirt.

Brad took monochrome to another level at the Once Upon A Time in Hollywood premiere wearing this tan-colored suit and shirt within the same color family. His hat and shoes perfectly matched the rest of his sartorial choice. How cool is he?

A smiley Brad looking handsomely stylish in a dark pea coat and newspaper boy hat is a look we stan!

Possibly one of the most elegant looks we’ve seen Mr. Brad Pitt wear is this tailored tuxedo he wore to the 2020 Oscars. The American actor gave this classic look a modern twist with a velvet jacket.