Brad Pitt, 56, is a chameleon when it comes to his style — and that’s usually because of the woman in his life! From dapper to casual, and clean cut to shaggy, the Oscar winner has changed up his look over the years and regularly matched his various exes including Jennifer Aniston, 51, Angelina Jolie, 45, Gwyneth Paltrow, 47, and Juliette Lewis, 47. See photos below of Brad dressing just like his famous gals over the years.
Jennifer Aniston
Jennifer and Brad were the golden couple of Hollywood! The pair married on July 29, 2000 after two years of dating, sadly splitting in 2005. Jen and Brad were a bonafide red carpet staple over their five year marriage, often slaying with their complimentary looks — including at the 2001 premiere of Brad’s movie The Mexican. The couple both opted for suits in a neutral color tone, with Brad rocking a head-to-toe camel look, and Jen for all-white. Her beige colored bag and t-shirt picked up on Brad’s ensemble, making for a picture-perfect moment.
Two years earlier, the couple showed off their similar looks again as they stepped out to the 1999 Emmy Awards! The two actors embraced a rock ‘n’ roll vibe for music’s biggest night, with Jenn ditching her signature pin-straight hair for a tousled curl, and Brad adding some texture to his. The Fight Club star also showed off some facial hair to change things up, a departure from his usual clean-shaven look at the time. Brad was dapper in an all-black suit, while Jennifer dazzled in a dress featuring a sequin bodice and chocolate brown skirt.
Brad and Jennifer twinned on another outing, stepping out in 2002 in blue jeans, brown leather shoes and t-shirts! The couple even matched with their hair, with Brad growing out his locks and embracing a natural wave just like his then-wife. Brad added a gray colored beanie to his ensemble, while Jennifer carried a neutral colored leather tote and taupe jacket.
Angelina Jolie
Shortly after his split from Jennifer, Brad was head-over-heels in love with his Mr. & Mrs. Smith co-star Angelina Jolie. By the time she linked up with Brad, Angelina appeared to have moved past her ’90s goth look (which peaked at the 2000 Oscars) and into a refined, classic style. All eyes were on the glamorous duo — who share kids Maddox, 19, Pax, 16, Zahara, 15, Shiloh, 14, and twins Vivienne and Knox, 12 — when they attended the Academy Awards back in 2009! Angelina slayed in an elegant strapless gown by Elie Saab, adding eye-catching pair of emerald drop earrings from jeweler Lorraine Schwartz. Brad echoed her red carpet look with a classic black tuxedo, also losing his past blonde highlights for his natural brunette tone just like Ang’s.
The pair also rocked sleek black ensembles for the 2007 premiere of Brad’s movie Oceans 13. Angelina sported a timeless black shift dress for the red carpet, while Brad mirrored her in a dark colored suit and black henley shirt. The pair were all-smiles as they posed for photographers in their monochromatic ensembles at the legendary Grauman’s Chinese Theatre! Sadly, this Hollywood power couple split in 2016 but are still working out their divorce.
Gwyneth Paltrow
Before Angelina and before Jen, Brad had a high-profile relationship with actress Gwyneth Paltrow. The pair met while filming movie Se7en, and were engaged in 1996 before ultimately splitting in 1997 (two years before she nabbed an Oscar for Shakespeare In Love). Over a decade before she founded lifestyle site Goop, GP was a trailblazer in fashion — even influencing then fiancé Brad. The blonde couple twinned in gold oval-shaped sunglasses featuring black lenses, styling their hair similarly and rocking complimentary colors at the Pallbearer premiere in 1996. Although the pair both moved on to subsequent marriages (and divorces), the couple had their fair share of memorable red carpet moments!
Juliette Lewis
Brad and Juliette Lewis’ romance began after filming the Lifetime movie Too Young to Die? in 1990. Juliette, now 47, dated the future Oscar winner for three years which included plenty of photo opps. The then-couple showed off their matching preppy looks when they stepped out for the premiere of A River Runs Through It back in 1992! A then-blonde Juliette kept her hair parted in the center just like Brad’s, as the pair both rocked white collar shirts.
