Reviving old school style with a modern twist? No one does it better than Sabrina Carpenter.
At the 2026 MTV Video Music Awards, held at the Peacock Theater in downtown LA on Sunday, September 27, the Manchild hitmaker stunned fans by bringing back Madonna’s iconic 1980’s retro look to the spotlight with a modern twist.
During the event, Carpenter joined the 68-year-old American singer-songwriter on stage to open the show with a performance of their duet song, Bring Your Love, which won them Best Collaboration honor.
While the collaboration itself brought together two generations of pop music, the Espresso singer’s outfit made the connection even clearer by taking inspiration from the fashion style that shaped Madonna’s early career.
Sabrina Carpenter’s Madonna-inspired VMAs 2026 look
Stepping onto the stage, Sabrina Carpenter dropped jaws in a sizzling a black beret, a white button-down shirt open over a bra and black sequined boyshorts held up by suspenders.
How Sabrina Carpenter’s style put a modern twist to Madonna’s iconic look – A then and now comparison
The outfit recalled Deborah Feingold’s 1982 photo shoot of Madonna, taken before her debut album was released.
For those unfamiliar, the Confessions II hitmaker’s early fashion was known for blending traditionally feminine pieces with rebellious details, from lace and lingerie-inspired styling to bold accessories and layered separates. Carpenter’s VMAs outfit captured the same essence.
Madonna’s 1982 photoshoot by Deborah Feingold captured her in an iconic look that included a simple white, oversized T-shirt contrasted sharply by thick black button-front suspenders and dark, high-waisted trousers, all complemented with military-style beret.
Giving it a playful and modern spin, Sabrina Carpenter replaced the white T-shirt with an open white button-down shirt, and layered it with a black lace bra.
She also replaced the high-waisted black trousers with sequined black shorts, tights, and wore a black beret.
Combining the outfit with black suspenders immediately recalled Madonna’s playful and rebellious style, sparking nostalgia.
