Sabrina Carpenter has got that blonde ambition.
Ever since the singer entered the pantheon of famous blondes, she’s been quick to reference her forebears through fashion. At the 2024 MTV VMAs, Carpenter and her stylist Jared Ellner achieved a two-for-one homage. In a silver beaded Bob Mackie dress from 1991, she pulled off a Russian nesting doll of nods, referencing Madonna referencing Marilyn Monroe. “It was originally designed for Madonna to wear to perform at the Academy Awards,” Alexis Novak, owner of Tab Vintage—where the dress was sourced—tells Vogue. “It was inspired by Marilyn Monroe in Gentlemen Prefer Blondes and made headlines when she wore it.”
That same night, Carpenter paid tribute to another famous blonde: Kate Moss. Heading to the VMA after-party, she rocked a sheer white lace minidress over white underwear, which she paired with teetering white platforms and a kiss-print purse. The dress, from Tom Ford’s spring 1996 Gucci collection, was originally worn on the runway by the supermodel.
A noted musical theater fan, Carpenter also incorporated some classic Hollywood references into her litany of Grammys looks. When she first hit the 2025 red carpet, she wore a pale blue custom JW Anderson dress complete with an ostrich feather trim. But the real star of the show was the massive pear diamond from Chopard, which hung down her bare back—a nod to Shirley MacLaine’s character Louisa May Foster in the 1964 film What a Way to Go!
It didn’t end at the carpet though. For her performance—a medley of songs from Short n’ Sweet—Carpenter practically floated downstairs in a sequined Dolce Gabbana tuxedo à la Goldie Hawn singing “Nobody Does It Like Me” on The Goldie Hawn Special.
With Carpenter’s repertoire of deep cuts and a clear appreciation for Hollywood history, we can’t wait to see what’s next.
