Brad Pitt, 62, Goes Full ‘Cool Dad’ on Date With Girlfriend Half His Age

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.

The once-popular styling hack saw a revival in 2025 and is seen on pop artists like Justin Bieber and Bad Bunny, both 32.

De Ramon, vice president of jewelry brand Anita Ko , wore blue jeans with a white cutout top with flower embroidery.

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.

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.

The ex-couple met on the set of their hit film Mr. & Mrs.