Rosie O'Donnell First Embraced Her Gray Hair In The Perfect Way
Rosie O'Donnell has been rocking her silver fox look for quite some time now. While she hasn't gone completely gray, she has just the right blend of dark and white tresses to pull off a pretty chic hairstyle. Fans have become accustomed to seeing what has become her signature look over the past few years that it raises the question: When exactly did Rosie O'Donnell first embrace her gray hair?
It turns out the former TV host began displaying a few subtle strands of gray around 2017 — for instance, as seen below, when she attended the Double Standards benefit concert celebrating women's rights on November 12, 2017, in New York City. O'Donnell was photographed backstage rocking shoulder-length brunette hair, with some gray hairs beginning to emerge by the hairline. It was evident then — as it is now — that she wasn't trying to cover up the transition, but instead embraced her gray hair in the perfect way.
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In the years that followed, O'Donnell pleasantly continued embracing this more mature image, displaying even more gray in 2019 for her role as Tutu on Showtime's dark comedy "SMILF." However, she did have to dye her hair as her natural gray hadn't all completely come through, and the actor admitted that not everyone was on board with her looking like a grandma. "I have five kids ... and three of them say you look way too old," O'Donnell told Today. "I have a six year old, who said to me, 'When you pick me up at school everyone thinks that you're the grandma.'" When O'Donnell asked her daughter for a solution, she snapped, "Make your hair black again!"
Rosie O'Donnell is still rocking her gray hair
Despite the push-back from her kids, O'Donnell has continued to rock her silver-stranded mane. Like many Hollywood celebs who have embraced their graying natural hair color, the "Now and Then" star doesn't seem interested in covering up the signs of aging.
Though she is embracing this new chapter in life, O'Donnell isn't about to let aging diminish her appearance or determine what she should look like as she gets older. In a May 2026 Instagram post, the actor revealed she had recently undergone a facelift. "I used to feel very strongly about facelifts. Not casually — morally. I had assigned myself as head of all women who would never — ever," she wrote.
However, O'Donnell, who underwent an undeniable 'Mounjaro face' transformation after taking the GLP-1 drug for her diabetes, said she lost 50 pounds, which led to severe loss of skin elasticity. "I'd look in the mirror and think, this isn't aging, this is ... melting with intention. I tried to be evolved about it and say things like, 'This is natural. This is earned.' And then ... 'umm how earned does it have to look?' There's a point where acceptance starts to feel like lying." The actor followed up a day later by sharing before-and-after pics, which you can see below.
