Hollywood veteran Brad Pitt and his 32-year-old girlfriend, Ines de Ramon, hit the town together in New York City on June 14.
Photographers captured Pitt, 61, wearing a striped button-up shirt, blue velvet blazer, baggy blue jeans, and black squared-toe shoes while rocking a low haircut.
The Oklahoma-born, Missouri-raised entertainer’s outfit was from Willy Chavarria’s fall 2025 menswear collection. Ramon showed up for the outing in NYC in a white, sleeveless outfit.
People on the internet became fixated on Pitt’s fashion choice. Instagram users offered their thoughts on the Academy Award winner’s choice of clothing for his date night with Ramon.
“Love his style usually, but that blazer is not right,” expressed a disappointed fan. A second comment read, “Sorry, Brad, but that outfit does you no favors! The hair has to go too!”
“Not a fan of him in that baggy velvet jacket,” someone conveyed. A more-irked observer declared, “That outfit is horrendous. Did he hire [Justin] Bieber’s stylist?”
One commenter on the social media app wrote, “He doesn’t look like Brad.” Additionally, one person stated, “Wow, the clothes, the lack of hair. What’s going on with him right now?”
“What is he wearing??? Looks awful when he can look good. She’s no oil painting either!” a Daily Mail reader exclaimed. Another posted, “Pitt is one ageing mess. And why is he being pap shot on a daily basis looking so cringey?”
Other people suggested Pitt was struggling with his identity and self-confidence after crossing the 50-year mark in his life. For instance, an online observer offered, “This is what a later life crisis looks like.”
However, a critic responded, “Yikes! We can’t even call it a midlife crisis. He is way too old for that! He looks awful and more so ridiculous with that woman. HE IS TRYING SO HARD TO BE SEEN AS YOUNG. You are not [in your] 40s anymore. This is just sad, and you look even older than 60. So please pack it in, Brad! Annie [can] at least say she had him at his best… or maybe Jennifer did lol!”
Pitt and Ramon’s romance started making headlines in November 2022 when they were spotted at a Bono concert in Los Angeles. By December of that year, an anonymous insider told People the pair were “dating and happy.”
The couple reportedly attended several industry events together in 2023 but chose to avoid the photographers outside the venues. Ramon finally made her red carpet debut with Pitt at the premiere for his “Wolfs” movie at the 2024 Venice Film Festival.
In September 2024, a Pitt associate claimed he began living with the jewelry industry executive in February of that year. The source said, “It started out as a fun and casual relationship, but after moving in together, they realized that they have something special.”
Rumors of possible marriage plans began to circulate, but a report in April 2025 claimed that the wedding is “on hold” because Ramon refused to sign a prenup agreement, which is apparently a “touchy subject” for them.
Previously, Ramon was married to “The Vampire Diaries” actor Paul Wesley. After three years of marriage, the University of Geneva graduate separated from Wesley in September 2022 before officially divorcing in February 2024.
Pitt has been married twice. The “Once Upon a Time in Hollywood” actor wed “Friends” star Jennifer Aniston, 56, in July 2000. After announcing their separation in January 2005, Pitt and Aniston finalized their divorce in October of that year.
“This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months,” they said in a joint statement.
Pitt started dating Angelina Jolie, 50, after meeting the Oscar-winning actress while filming the 2004 action movie “Mr. & Mrs. Smith.” He was still married to Aniston at the time. Pitt and Jolie eventually tied the knot in August 2014.
The celebrity couple, once collectively known as Brangelina, share six children. In 2016, Jolie filed for divorce following an altercation on a private plane flight. Despite allegations of physical abuse, federal and local investigations ended without any formal charges.
Pitt and Jolie were declared legally single in 2019. A long legal battle between the “By the Sea” co-stars came to an end in December 2024 once their divorce was finalized.
Meanwhile, Pitt leads the upcoming “F1” sports drama alongside Damson Idris, Kerry Condon, Tobias Menzies, and Javier Bardem. The Joseph Kosinski-directed motion picture is scheduled to debut in North American theaters on June 27.
