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Brad Pitt’s style evolution over the years, from casual to dapper: how he went from jeans, tees and blond hair in the 90s, to suits on the red carpet, to breaking the internet with bold looks at 60

Hollywood A-lister Brad Pitt has evolved his style from laid-back to sophisticated over the decades. Photo: Getty Images
Brad Pitt, one of Hollywood’s most prominent actors, was 27 when he got his first big break on Thelma & Louise in 1991.

As the actor celebrates his 60th birthday this December, let’s look back at how his style has evolved over the years.

Brad Pitt’s laid-back vibes

Brad Pitt sporting a casual ensemble under his leather jacket in his early days. Photo: Getty Images

The actor and producer had already established the laid-back aesthetic in the early days of this career. At the Red Heat premiere in 1988, the then 24-year-old-actor wore a casual ensemble of jumper and trousers under a leather jacket.

Denim ruled during Brad Pitt’s Thelma & Louise phase. Photo: Getty Images

Pitt was 27 when he landed a role in the 1991 adventure thriller movie Thelma & Louise. The film was a pivotal point in his career and launched him to stardom.

At the movie’s premiere, the actor sported a denim-on-denim look under an oversized blazer. He wore his favourite suede shoes and accessorised with a pair of round sunglasses.

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He had long hair for a while

Brad Pitt went hippy for a while and let his hair grow. Photo: Getty Images

Later, the actor channelled some serious hippy vibes with oversized clothes and his beach blonde hair falling below his shoulders.

And then came the ponytail. Brad Pitt in the mid-1990s. Photo: Getty Images

At the premiere of the classic 1994 movie Interview with a Vampire, Pitt kept it casual in a button-up shirt, loose trousers and a leather jacket. He wore his beach blond hair in a dishevelled ponytail.

He eventually got a much needed haircut

Brad Pitt cleaned up pretty good and took his casual style to new heights. Photo: Getty Images

After filming 1995’s Legends of the Fall, the actor chopped off his long locks and went back to his elevated casual style.

The early 2000s baggy pants

With the new millennium, Brad Pitt’s pants got baggier. Photo: Getty Images

Pitt’s pants started getting baggier in the early 2000s.

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Jennifer Aniston and Brad Pitt in 2000. His pants got even baggier! Photo: Latsi

And baggier.

From jeans to suits on the red carpet

Brad Pitt was known for dressing down in denims, a tee and a leather jacket, even on the red carpet. Photo: Getty Images

Pitt was infamous for dressing down for the red carpet in his earlier days.

This particular outfit he wore to the Mr & Mrs Smith Los Angeles premiere in 2005 shows the actor’s dedication to live up to that reputation.

Pitt retired his trusty blue jeans and leather jacket in exchange for fitted suits in 2009.

Brad Pitt with Angelina Jolie. The Hollywood star moved up to suits, ties and scarves. Photo: Getty Images

Pitt’s style changed drastically in the late 2000s. He ditched his baggy jeans and bottle blonde hair for a suit and tie. He also started accessorising more with scarves and hats.

Brad Pitt at a photo call during the Cannes Film Festival in Cannes, France, in 2011. Photo: EPA

The actor looked dapper in a salmon suit at the 62nd Cannes Film Festival in May 2011. He accessorised with a grey scarf and a pair of tinted shades.

Hats, hats, hats

Brad Pitt keeps it rugged with suede and sunglasses. Photo: Getty Images

Pitt brought back his staple suede shoes for this all white-look in 2016. He accessorised with a hat and pair of sunglasses.

Brad Pitt’s gem-toting plaid shirts even use diamonds for buttons

Brad Pitt attends a red carpet for the Quentin Tarantino film, Once Upon a Time in Hollywood, in Mexico City, in August 2019. Photo: AFP

For the premier of Once Upon a Time in Hollywood in 2019, the actor channelled the old money aesthetic in a monochromatic outfit complete with a matching hat.

His fashion choices in 2022 broke the internet

Brad Pitt walks the red carpet for the movie Bullet Train at the Zoopalast, Berlin, in July. Photo: AP
Pitt broke the internet when he showed off his sculpted legs in a thigh-skimming midi skirt during the Berlin premiere of his 2022 film Bullet Train.

He’s been dressing in flashier colours

Brad Pitt is seen arriving at his trailer in January, in New York. Photo: GC Images
Pitt stepped out onto the streets of New York in a bright orange puffer jacket from Moncler and a green beanie in January this year.
As he turns 60, Brad Pitt keeps his style casual. Photo: Getty Images

At 60, the actor looks as youthful as ever. His relaxed fits and baggy jeans have made a comeback.

  • Once known to dress down for the red carpet and letting his hair grow out hippy-style, Brad Pitt can definitely do sophisticated fashion too – but doesn’t shy away from bold colour at 60
  • The Hollywood A-lister loves hats, scarves and suede shoes too, and stepped out in New York recently in an orange Moncler jacket and green beanie – then there was the leg-baring skirt look …