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

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?

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.”