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Gwyneth Paltrow shows off a dress she wore on a date with Brad Pitt

Paltrow and Pitt were an "It Couple" in the mid-90s until their split in 1997.
Brad Pitt and Gwyneth Paltrow on Madison Avenue, NYC
Brad Pitt and Gwyneth Paltrow strolling on Madison Avenue on August 3, 1996.Lawrence Schwartzwald / Getty Images
/ Source: TODAY

Gwyneth Paltrow gave fans a blast from her romantic past with a tour of her fashion archive.

Paltrow took viewers through her archival closet in a video on Goop’s YouTube channel. She pulled recent items from her brand’s label as well as pieces from her 90s wardrobe, including one iconic look she wore while dating Brad Pitt. 

Early in the video. the actor pulled a white shirtdress from the racks, which she wore to the premiere of “The Pallbearer” with Pitt in 1996.

“This is a 90s Calvin Klein dress, I think I wore to a premiere of something when I was going out with Brad Pitt,” she described the piece. “Very 90s, you know, shirtdress kind of thing. It’s slouchy, it’s relaxed, it’s giving that very 90s ‘I don’t give a f---.’”

Paltrow and Pitt first began dating in 1994 and even rocked matching haircuts at one point in their relationship. The couple got engaged in December 1996, but ultimately split in 1997.

While reflecting on their breakup during a January 2015 interview with Howard Stern, Paltrow said, “I was such a kid — I was 22 when we met…You can’t make that decision when you’re 22 years old. … I wasn’t ready, and he was too good for me.”

Pitt was married to Jennifer Anniston from 2000 to 2005 and Angelina Jolie from 2014 to 2019, while Paltrow was married to Coldplay frontman Chris Martin from 2003 to 2016 before she tied the knot with current husband Brad Falchuk in 2018.

Despite their split more than two decades ago, Paltrow and Pitt still look back fondly on their time together. 

During an October 2022 interview with ET Canada, the “Shakespeare in Love” star spoke about her lasting admiration of her ex and how their friendship has evolved over time.

“When we first broke up, we weren’t friends for a while and then we sort of found our way back, probably about 18 or 19 years ago, something like that, and then just kind of stayed in touch over the years,” Paltrow said. “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.”

Paltrow also hosted Pitt in an interview in June 2022 for her website Goop about his new clothing line. During their conversation, the couple rehashed details from the past, including his relationship with her late father, Bruce Paltrow, who died in 2002.

“I’ll never forget when we were engaged and he came to me one day, his eyes full of tears, and he said, ‘You know, I never really realized what they mean when they say you’re gaining a son. Like, I’m gaining a son,’” Paltrow said before asking Pitt, “What impact did he have on you? Why did you love him, even though we didn’t get married, unfortunately?”

After exchanging “I love yous,” Pitt said what he loved the most about her father was that he encouraged her to be independent and have a voice. The actor added, “He carved the way for you guys to be who you are. And I think that’s so important to parenting, you know?”

“So the child is free to find out who they are and what they love and what they don’t,” he said. “You guys were just so free in your conversations. And witty. And intelligent. And funny as f---."