Brad Pitt, 62, Goes Full ‘Cool Dad’ on Date With Girlfriend Half His Age
The father of six busted out his backward hat for the occasion.
JB Lacroix/FilmMagic/Getty Images
Actor Brad Pitt is breaking out his very best “cool dad” outfits for his latest dates with age-gap girlfriend Ines de Ramon.
The 62-year-old father of six sat down to watch the U.S. Open Men’s Singles Championship game in Flushing, New York, on Sunday, Sept. 13. In the Emirates suite sat de Ramon, his 33-year-old jewelry designer girlfriend.
Pitt wore a blue button-up shirt with matching pants, accessorized with a golden beaded bracelet and necklace, a Patek Philippe watch, and aviator sunglasses.
The main attraction of his outfit, however, was the navy-blue cap that the Oscar winner styled backward.
Brad Pitt styled his hat backward for the U.S. Open. Here with Ines de Ramon before the men’s singles final match between Ben Shelton of the U.S. and Germany’s Alexander Zverev.
Mike Segar/Reuters
The once-popular styling hack saw a revival in 2025 and is seen on pop artists like Justin Bieber and Bad Bunny, both 32.
Brad Pitt and Ines de Ramon at the U.S. Open.
Courtesy of Emirates
De Ramon, vice president of jewelry brand Anita Ko, wore blue jeans with a white cutout top with flower embroidery.
Ines de Ramon and Brad Pitt at the U.S. Open in Flushing Meadows, New York, on Sept. 13, 2026.
Mike Segar/Reuters
The couple, who are 29 years apart in age and have dated for four years, also watched the women’s singles final together on Saturday, Sept. 12.
Ines de Ramon and Brad Pitt at the U.S. Open on Saturday, Sept. 12.
Courtesy of Emirates
For the occasion, Pitt wore a light blue polo shirt, aviators, and a denim cap worn backward, while De Ramon wore a vintage John Galliano newspaper dress reminiscent of Carrie Bradshaw’s Christian Dior frock in Season 3 of Sex & the City.
Pitt shares six children with his ex-wife, Oscar-winning actress Angelina Jolie, 51.
Angelina Jolie and Brad Pitt at the 64th annual Golden Globe Awards in Beverly Hills, California, in January 2007.
Lucy Nicholson/Reuters
The ex-couple met on the set of their hit film Mr. & Mrs. Smith in 2004. After roughly 10 years together, they married in August 2014.
The marriage ended just two years later, when Jolie filed for divorce in September 2016, citing irreconcilable differences.
Angelina Jolie with Shiloh, Zahara, Vivienne, Maddox, and Knox at the "Eternals" UK Premiere in October 2021 in London, England.
Karwai Tang/WireImage
After the highly publicized divorce, which dragged on until a 2024 settlement, several of their children chose to drop Pitt from their last name.
After turning 18 in 2024, their daughter Shiloh, now 20, legally changed her last name to Jolie.
Three of her siblings followed suit: In 2026, Maddox, 25, Zahara, 21, and Vivienne, 18, all petitioned to drop Pitt from their last name.
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Jolie and Pitt also share Pax, 22, and Knox, 18, who still legally go by Jolie-Pitt.
Brad Pitt and Jennifer Aniston at the 51st Annual Emmy Awards in Los Angeles in 1999.
Fred Prouser/Reuters
Before his relationship with Jolie, Pitt was married to Friends star Jennifer Aniston, 57, from 2000 to 2005.
Although both Jolie and Pitt denied having an affair, Jolie told The New York Times in 2006 that they “fell in love” on the set of Mr. & Mrs. Smith.
De Ramon was previously married to The Vampire Diaries actor Paul Wesley, 44, whom she wed in February 2019. The couple separated in April 2022 and finalized their divorce in February 2024.
Paul Wesley and Ines de Ramon attend the Mercy For Animals Gala in Los Angeles on September 14, 2019. The couple were married from 2019, but separated just three years later.
Alberto E. Rodriguez/Getty Images
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