5 times Brad Pitt copped his partner’s style for matching couple looks – from dark and moody with Angelina Jolie and 90s fashion with Jennifer Aniston, to twinning blond hair with Gwyneth Paltrow

Dec 12 , 2023

Whether out and about with his former partners Jennifer Aniston, Angelina Jolie or Gwyneth Paltrow, Brad Pitt has made a habit of mimicking the style of the woman he’s married to or dating at the time. Photos: Getty Images

He’s one of the highest paid actors in the world and has been voted People magazine’s Sexiest Man Alive twice (in 1995 and 2000), but when it comes to his style, it seems Brad Pitt follows the lead of the special women in his life.

From his early days of dating Juliette Lewis and Gwyneth Paltrow to later marrying Jennifer Aniston and Angelina Jolie, Pitt seems to have penchant for looking like the significant other in his life. We may even be seeing more couple looks involving Pitt, as he started dating jewellery designer Ines de Ramon in late 2022.

But for now, let’s take a walk down memory lane …

1. Christina Applegate (1988-89)

Christina Applegate is said to have ditched Brad Pitt in favour of Canadian rocker Sebastian Bach

Back in the late 80s, when they were both budding actors, Christina Applegate and Pitt were an item. While they largely kept things casual, the pair were photographed getting close numerous times between 1988 and 1989, including at an Amnesty International event and the 1989 MTV Video Music Awards (VMAs), which they attended together.

In their short time together, the pair embraced the same trends from the era, often sporting similar messy hairstyles and 80s blue jeans. Sadly for Pitt, Applegate ditched him for Canadian rocker Sebastian Bach, per InStyle.

2. Juliette Lewis (1989-93)

Juliette Lewis met Pitt, then 27, when she was just 17, on the set of Too Young to Die

Of all Pitt’s past relationships, his romance with Juliette Lewis is perhaps the most unlikely pairing. Actress turned rock star Lewis was only 17 when she met 27-year-old Pitt on the set of Too Young to Die, but the co-stars quickly grew close and started dating.

And they must have been smitten – because they quickly started sharing the same style too, from casual gear on nights out to matching suits on the red carpet. And it didn’t stop there. Both Lewis and Pitt sported similar middle-parted blond locks during their time together.

“It was such a lovely time in my life – well, in both of our lives – because we were anonymous,” Lewis told BlackBook in 2009. “For half of our relationship we were just unknown young actors in LA.”

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3. Gwyneth Paltrow (1994-97)

After meeting Gwyneth Paltrow on the set of Seven, Pitt and the actress ended up getting nearly identical hairstyles

Way before Gwyneth Paltrow was “consciously uncoupling”, she was apparently all about matching couple style. Paltrow and Pitt started dating in 1994 after meeting on the set of Seven, with the actor eventually proposing in 1996. They never made it down the aisle, but their time together brought the world plenty of matching couple looks to remember.

Not only did they twin their outfits and accessories, they even shared matching hairdos. Paltrow later revealed on Instagram that the identical hairstyles were unintentional, but were cut by the same hairdresser – celebrity hairstylist Chris McMillan. These days, the exes are still close friends, with Paltrow telling Entertainment Tonight last year: “I adore him. He’s an amazing person and he’s a great entrepreneur, and such a creative, and such a good person. I really love him. I’m a big fan.”

4. Jennifer Aniston (1998-2005)

At the peak of her Friends fame when she began dating Brad Pitt, Jennifer Aniston’s style visibly rubbed off on the actor

Considering Pitt’s seeming love for couple style, it’s only fitting that he matched looks with Jennifer Aniston during their time together. Once Hollywood’s golden couple, the pair regularly rocked matching outfits both on and off the red carpet. From their baggy cargo pants, bomber jackets and matching eyewear to colour-coordinated suits and similar sun-kissed hair, Brad and Jen oozed 90s style in unison.

We all know what happened after their marriage came to screeching halt in 2005, but after all these years, Jen and Brad are finally on good terms again. “Brad and I are buddies. We’re friends,” Aniston told Howard Stern in 2021 after the former couple appeared at a fundraising table read of Fast Times at Ridgemont High. “We speak, and there’s no oddness at all – except for everyone who probably watched it and was wanting there to be, or assumed there to be,” Aniston said. “We had fun, and it was for a great cause.”

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5. Angelina Jolie (2004-16)

Brad Pitt went through a phase of wearing darker clothes – and even sported darker hair followed by lighter hair again – in line with the style choices of then-partner Angelina Jolie

When Pitt started dating Angelina Jolie amid a media frenzy, not only did his life change – so did his style. Matching his girlfriend’s look, Pitt started sporting a darker hairstyle around the same time Jolie embraced her natural brunette hair in 2006. Years later, when Angelina experimented with a lighter honeycomb hair colour in 2013, Pitt also went back to blond. Over the years, they twinned everything from secret-agent sunglasses, matching long hair and sleek suits, to countless coordinated red carpet outfits.

But no amount of matching looks could keep them together, with the pair splitting up in 2016. They have been embroiled in a nasty custody battle ever since.

Celebrity style

From his days of relative anonymity in the 1980s to his highly publicised marriages, Brad Pitt has shown a fondness for aping his significant others’ looks, from outfits to hairstyle
Having once matched with Gwyneth Paltrow and Jennifer Aniston, Pitt is now dating Ines de Ramon, in his first serious relationship since his divorce – so could his next couple looks be on the horizon?