Sabrina Carpenter and Halsey Serve Vintage Glam in Iconic Gowns Once Worn by Superstars
Nothing captures the magic of vintage fashion quite like wearing a piece previously graced by a legendary icon.
At the MTV Video Music Awards on September 11, Sabrina Carpenter not only wowed with her extraterrestrial antics but also stole the spotlight on the red carpet with a stunning fashion throwback. The "Espresso" singer dazzled in a strapless, V-neckline Bob Mackie gown, lavishly adorned with sequins, pearls, and crystals—a piece originally worn by Madonna back in 1991.
Bob Mackie himself took to Instagram to share the gown’s storied history, revealing that Madonna first wore a sample of this show-stopping dress for a Vanity Fair cover shoot. Shortly after, the "Material Girl" called Mackie to request a custom version for the 1991 Academy Awards, inspired by Marilyn Monroe’s iconic look in Gentlemen Prefer Blondes.
Madonna not only wowed audiences at the Oscars in this sparkling number while performing Stephen Sondheim’s “Sooner or Later” from Dick Tracy—which won the award for Best Original Song—but also made headlines by attending the event with Michael Jackson, making the night unforgettable. She later donned the custom gown in a provocative photo shoot for her controversial book Sex.
Fast forward more than three decades, and Sabrina Carpenter brought the vintage magic back to life at the VMAs, channeling her inner bombshell while accepting her award for Song of the Year. Wearing the sample version of the dress, which her stylist Jared Ellner sourced from Tab Vintage, a go-to for archival celebrity fashion, Carpenter proved that some styles are truly timeless.
Tab Vintage’s owner, Alexis Novak, spoke to Vogue, sharing that while Madonna still has the custom Mackie gown in her personal archive, Carpenter wore the other sample version. “Madonna still has the custom gown Bob Mackie made for her in her archive, but the other sample piece is the dress I believe we have,” Novak explained.
But Carpenter wasn’t the first to give this dress a second life. Before her, the iconic gown was also worn by Fran Drescher’s beloved character Fran Fine on The Nanny in 1994, adding yet another layer to its legendary status.