The pop icon supported Britney Spears’ latest fashion collaboration with Gucci’s Demna, wearing a nostalgic tee from ...

To complete her look, Madonna layered the merch under an oversize denim jacket, which she paired with distressed jeans that featured a tear along one of the knees (Spears, of course, knows a thing or ...

Britney Spears, Madonna, and Christina Aguilera perform onstage during the 2003 MTV Video Music Awards at Radio City Music Hall on August 28, 2003 in New York City. (Scott Gries/Getty Images) ...

Britney leaving Kabbalah didn’t hurt their relationship, though, and when the teen pop star struggled during the mid-2000s due to her fame, it was something Madonna could relate to.

Adopted by Madonna and Guy Richie at one year old, the now 18-year-old participated in New York Fashion Week 2024 via Off-White’s spring 2025 presentation, attended by Mary J. Blige, Issa Rae ...