Look of the Week: Sabrina Carpenter honors Madonna in vintage Oscars gown

Editor’s Note: Featuring the good, the bad and the ugly, ‘Look of the Week’ is a regular series dedicated to unpacking the most talked about outfit of the last seven days.

Madonna was everywhere at this year’s MTV Video Music Awards in New York — and she wasn’t even there.

On Wednesday evening’s red carpet, Addison Rae and Anitta both wore bridalwear looks evoking the star’s performance of “Like a Virgin” at the very first VMAs, almost 40 years ago to the day. But it was Artist of the Year nominee Sabrina Carpenter who went the extra mile by tracking down a vintage gown from the Queen of Pop’s style archive.

Featuring a deep-V neckline and embellished with sequins, pearls and crystals, the white satin gown was designed — and later customized for Madonna — by celebrated fashion designer Bob Mackie. She famously wore it to the 1991 Oscars, which she attended alongside Michael Jackson before performing “Sooner or Later,” a song from the movie “Dick Tracy.”

And if the strapless look oozed old Hollywood glamour, that may be because Madonna had herself worn it as a tribute to Marilyn Monroe.

The dress was a reworked version of a dress that Madonna had earlier appeared in for a Vanity Fair cover shoot with photographer Steven Meisel. Acknowledging Carpenter’s homage, 84-year-old Mackie recounted the story via his official Instagram account on Wednesday night.

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

He also noted that the Queen of Pop later donned the figure-hugging dress in the pages of her controversial and wildly popular 1992 coffee table book, “Sex.” The gown was subsequently worn by Fran Drescher during a 1994 episode of “The Nanny.”

Mackie designed red carpet looks for some of the 20th century’s biggest stars, including Monroe, Diana Ross and Cher, for whom he produced the iconic towering headdress worn to the 1986 Oscars. Gowns from his archive have made a comeback in recent years, with Anya Taylor-Joy, Katy Perry, Zendaya and Miley Cyrus all seen sporting pieces from his archive on the red carpets. Kim Kardashian also controversially wore a dress Mackie sketched for Marilyn Monroe to the Met Gala in 2022 (a wardrobe choice Mackie called a “big mistake,” telling Entertainment Weekly at the time: “It was designed for (Monroe). Nobody else should be seen in that dress.”)

Carpenter’s stylist, Jared Ellner, said on Instagram that he acquired the Madonna gown through LA vintage clothing studio, Tab Vintage. He completed her look with a diamond necklace and other jewelry from De Beers.

Tab Vintage’s founder Alexis Novak told Vogue that Ellner and Carpenter had approached her with a “really incredible moodboard.” She added: “We sent them a deck of pieces we had in that vein and we’re so happy with what she decided on!”

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

After her showstopping red carpet arrival, she went on to perform a medley of her hits “Espresso” (which later won the VMA for Song of the Year), “Please Please Please” and “Taste.”

By that point, she had undergone a costume change, trading her vintage Mackie gown for a corseted bodysuit designed by Victoria’s Secret. But her on-stage outfit, which took over 180 hours to make and featured 18,500 hand-applied crystal beads, was very much in keeping with its shimmering predecessor.

And Carpenter wasn’t done with the Madonna references. Unless, of course, the kiss she shared with a dancer in an alien costume only coincidentally resembled the star’s embrace with Britney Spears at 2003’s VMAs (though her performance’s earlier reference to “Oops!… I Did It Again” suggested that Carpenter may have been playing Spears’ role at that point).

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