Look of the Week: Sabrina Carpenter Honors Madonna with a Vintage Oscar Dress

Madonna was everywhere at this year’s MTV Video Music Awards in New York, despite not even attending the event.

On the red carpet Wednesday night, stars like Addison Rae and Anitta donned bridal-inspired looks that echoed Madonna’s iconic “Like a Virgin” performance from the first-ever VMAs nearly 40 years ago. But it was Sabrina Carpenter, nominated for Artist of the Year, who took it a step further by wearing a vintage dress from the Queen of Pop’s fashion archive.

The satin white gown, adorned with sequins, pearls, and crystals, featured a plunging V-neckline. It was originally designed and customized for Madonna by famed fashion designer Bob Mackie. She wore it to the 1991 Oscars, where she arrived with Michael Jackson and later performed “Sooner or Later” from the film Dick Tracy.

The strapless dress exuded Old Hollywood glamour, fitting as Madonna herself had worn it as a tribute to Marilyn Monroe.

This gown was actually a reworked version of one Madonna previously wore for a Vanity Fair cover shoot with photographer Steven Meisel. To celebrate Carpenter’s tribute, Mackie, now 84, shared the story on his official Instagram Wednesday night.

“Maria Schiavo, a well-known fashion stylist, borrowed a sample of this dress for a Vanity Fair cover shoot with Madonna,” Mackie recalled. “Less than a week later, Madonna herself called to request her own version of the dress for the 1991 Oscars.”

He also noted that Madonna later wore the form-fitting gown in her infamous 1992 coffee table book Sex. Fran Drescher even sported it in a 1994 episode of The Nanny.

Mackie has designed red carpet looks for some of the biggest stars of the 20th century, including Monroe, Diana Ross, and Cher, for whom he created the iconic feathered headdress worn at the 1986 Oscars. Pieces from his archive have made a resurgence in recent years, with stars like Anya Taylor-Joy, Katy Perry, Zendaya, and Miley Cyrus donning his designs on red carpets. Kim Kardashian also controversially wore a Mackie-designed dress originally made for Monroe to the 2022 Met Gala—a choice Mackie criticized as a “big mistake,” telling Entertainment Weekly: “It was designed for (Monroe). No one else should wear that dress.”

Sabrina Carpenter’s stylist, Jared Ellner, revealed on Instagram that he sourced Madonna’s vintage dress from Los Angeles-based Tab Vintage. Carpenter completed the look with diamond jewelry from De Beers.

Tab Vintage founder Alexis Novak told Vogue that Ellner and Carpenter approached her with a “really incredible mood board.” She added, “We sent them a selection of pieces in that style, and we’re thrilled with what they chose.”

It was a big night for Carpenter, who was nominated for seven awards following a breakthrough year that saw her top the Billboard 200 albums chart for the first time.

After her dazzling red carpet entrance, she delivered a medley of hits, including “Espresso” (which went on to win the VMA for Song of the Year), “Please Please Please,” and “Taste.”

By then, she had swapped her vintage Mackie gown for a corseted bodysuit designed by Victoria’s Secret. But her stage outfit, which took more than 180 hours to create and featured 18,500 hand-applied crystal beads, echoed the brilliance of her earlier look.

And Carpenter wasn’t done with her Madonna tributes. Unless, of course, the kiss she shared with a dancer dressed as an alien was purely coincidental and not a nod to Madonna’s famous kiss with Britney Spears at the 2003 VMAs—though her earlier performance of “Oops!… I Did It Again” hinted that Carpenter may have been channeling Spears in that moment.

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