Brad Pitt Channels His Mid-Aughts Look With Major Hair Transformation

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Brad Pitt Set to Star in New 'Once Upon a Time in Hollywood' Movie

Even Brad Pitt is tapping into the Y2K trend.

Just as low-rise jeans and baby tees are making a comeback, so is one of the Once Upon a Time In Hollywood star's most iconic looks of the 2000s.

Ditching his signature blonde locks, Brad was recently seen driving around Los Angeles while sporting a clean buzzcut similar to the one he rocked during the early aughts. And just like his Tyler Durden character in 1999's Fight Club, the 61-year-old capped off the look with large sunglasses.

While Brad has undergone many hair transformations throughout the years, his buzzed head is possibly one that stands out among the rest. After all, his then-girlfriend Jennifer Aniston was the one who shaved it all off for his role in Fight Club.

The Oscar winner went on to grow his hair out in the time for the film's October 1999 premiere—as well as his July 2000 wedding to the Friends actress—before shaving it all off again during the mid-aughts to film 2005's Mr. & Mrs. Smith, where he met his second wife Angelina Jolie. (They split in 2016.)

But these days, Brad's style is centered more around practicality. "You get older, you get crankier, and comfort becomes more important," he quipped to Esquire in 2021. "I think it’s as simple as that."

And he doesn't want to hide his age, either.

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"I don't want to be running from aging," he said in a 2022 interview with Vogue. "It’s a concept we can’t escape, and I would like to see our culture embracing it a bit more, talking about it in those terms."

Describing "anti-aging" as "ridiculous," Brad continued, "I think that we’re learning that if we love ourselves, if we treat ourselves a little better, then there are long-lasting benefits to that. So just age healthy, age in a healthy manner."

To see more dramatic celebrity hair transformations, read on.

Jamie McCarthy/WireImage; Matt Baron/BEI/Shutterstock

Sebastian Stan

The Marvel actor said goodbye to Bucky Barnes' signature long hair in April 2025, showing off a shaved head at the Los Angeles premiere of Thunderbolts*.

Jon Kopaloff/Getty Images; Steve Granitz/FilmMagic

JoJo Siwa

In March 2025, the "Karma" singer debuted her rainbow mohawk at the GLAAD Media Awards. 

Instagram; TikTok

Emily Ratajkowski

In a March 2025 TikTok video, the model called this 'do with shaggy bangs the "worst haircut of my life."

Instagram / Gypsy Rose Blanchard

Gypsy Rose Blanchard

The Gypsy Rose: Life After Lockup star debuted a short bob in March 2025, more than two months after giving birth to her and fiancé Ken Urker's first child, daughter Aurora Urker.

Clifton Prescod/Bravo/Charles Sykes

Whitney Rose

The formerly blond Real Housewives of Salt Lake City star debuted a red bob on Watch What Happens Live in January 2025.

Instagram / Hailey Bieber

Hailey Bieber

The model debuted lighter locks in September 2024, a month after giving birth to her and Justin Bieber's first baby, son Jack Blues Bieber.

Pascal Le Segretain/Getty Images/Araya Doheny/FilmMagic

Lily Collins

The Emily in Paris star debuted her dramatic transformation at the world premiere of her new horror movie, MAXXXINE, in June 2024. 

"Changing my hair always brings out different sides of my personality and I love playing around," Lily told Vogue. "This cut and color feels bolder and yet somehow lighter. And completely more me—right now."

Sean Zanni/WireImage/John Nacion/Variety via Getty Images

Katie Holmes

While attending Chanel's Tribeca Film Festival Artists dinner in June 2024, Katie debuted a subtle, yet striking transformation of rich caramel balayage highlights that were blended throughout her brunette tresses.

Kylie Jenner / Instagram

Kylie Jenner

The Kardashians star debuted a platinum blonde look and a bob haircut after rocking waist-length strands for quite some time.

"Did someone say they missed king kylie," Kylie teased in the caption of her June 8 Instagram post, to which her sister Khloe Kardashian cheekily replied, "I did! I did!!!!!!"

Gilbert Flores/Variety via Getty Images/Pierre Suu/Getty Images

Lisa Rinna

The former Bravo star debuted a platinum blonde look during 2024 Paris Fashion Week Haute Couture.

Elisabetta Villa/Getty Images for Bulgari/Prodip Guha/Getty Images

Priyanka Chopra

The Heads of State star debuted a drastic haircut—a shoulder-grazing bob—while attending a Bulgari event in Rome i May 2024. 

TikTok / Jessica Biel

Jessica Biel

In May 2024, the actress chopped her hair into a bob that many fans on social media said reminded them of one of the looks she sported as Mary Camden on the '90s series 7th Heaven.

Instagram / Megan Fox

Megan Fox

The Transformers actress returned to her dark brown tresses and debuted a sassy bob in May 2024, a month after she dyed her hair blue to enter what she dubbed her "Jedi era."

Stephen J. Cohen/Getty Images

Dannielynn Birkhead

At age 17, the daughter of the late Anna Nicole Smith debuted a new lob hairstyle overnight during 2024 Kentucky Derby weekend, which she attended with dad Larry Birkhead.

Emma McIntyre / Getty Images for Baby2Baby / Instagram / Demi Lovato

Demi Lovato

The singer debuted a lighter, shorter 'do in April 2024.

Kelly Osbourne/Instagram

Kelly Osbourne

The Fashion Police alum debuted a blonde bombshell hair transformation May 8.

Vivien Killilea / Getty Images for Homeboy Industries / Chip Somodevilla / Getty Images

Kim Kardashian

Back to blonde: Kim debuted a new platinum 'do in April 2024.

Michael Buckner/Variety via Getty Images/Neil Mockford/WireImage

Rihanna

The Fenty Beauty founder debuted a bright blonde hair transformation April 17 while celebrating her latest Fenty x Puma collection in London.

Stefanie Keenan/Getty Images for FRAME/Michael Buckner/Variety via Getty Images

Delilah Belle Hamlin

The model debuted a bleach blonde pixie cut at the FRAME event April 4.

Megan Fox/Instagram/Dimitris Giannetos/Instagram

Megan Fox

The Jennifer's Body star traded in her bubblegum pink tresses for a baby blue bob, which she debuted April 2.

James Gourley/Getty Images/Jeff Kravitz/FilmMagic

Zendaya

Less than a month afer chopping her hair into a long bob, Zendaya debuted a honey blonde transformation at the Challengers premiere March 26.

Elle Fanning / Instagram

Elle Fanning

The Great star ushered in spring with a fresh cut, as she debuted a long bob March 25.

John Nacion/Getty Images/John Nacion/Getty Images

Rachel McAdams

The Mean Girls alum swapped out her signature blonde hair for a dark brunette transformation on March 18.

Vivien Killilea/Getty Images for Forever 21/Rachpoot/Bauer-Griffin/GC Images

Bre Tiesi

The Selling Sunset star looked completely unrecognizable after debuting a dramatic blonde transformation March 16.

Instagram/Kelly Osbourne

Kelly Osbourne

The Fashion Police alum ditched her signature purple hair after six years, tinting it an icy silver in March 2024. 

Unique Nicole/FilmMagic/Frazer Harrison/Getty Images

Zendaya

The Dune actress debuted a shoulder-grazing bob at Essence's Black Women in Hollywood Awards March 7.

Dominique Charriau/WireImage/Steven Simione/WireImage

Sydney Sweeney

The Anyone But You star made a showstopping appearance at Miu Miu's fall/winter 2024-2025 show during Paris Fashion Week. For the March 5 event, she unveiled a dramatic long bob haircut.

Hoda Davaine/Dave Benett/Getty Images/Jon Kopaloff/Getty Images for Max Mara

Zoey Deutch

To prepare for her upcoming role as  Jean Seberg, the 29-year-old debuted a bleached blonde pixie cut.

Monica Schipper/Getty Images/Leon Bennett/GA/The Hollywood Reporter via Getty Images

Anne Hathaway

The Princess Diaries alum unveiled fringe bangs at the 2024 Film Independent Spirit Awards.

Steve Granitz/Getty Images / Jon Kopaloff / WireImage

Selena Gomez

The star debuted a bangin' new style at the premiere of her friend Nicola Peltz Beckham's film Lola in February 2024.

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