The actor and producer had already established the laid-back aesthetic in the early days of this career. At the Red Heat Premiering 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 film 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 favorite suede shoes and accessorized 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 channeled 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 blonde hair in a braided 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 Fallthe 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 living 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 dyed his baggy jeans and bottle blonde hair for a suit and tie. He also started accessorizing 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 accessorized with a gray 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 accessorized with a hat and pair of sunglasses.

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

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Brad Pitt walks the red carpet for the film Bullet Train at the Zoopalast, Berlin, in July. Photo: AP

He’s been dressing in flashier colors

Brad Pitt is seen arriving at his trailer in January, in New York. Photo: GC Images
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.