Madonna’s most iconic VMAs looks through the years

See more of our coverage in your search results. Madonna is ready to strike a pose on the VMAs stage again. The Queen of Pop will open the VMAs 2026 on Sunday, Sept. 27, returning for her first performance at the show in 23 years. She’ll be joined by “special guests,” rumored to include Charli XCX and Sabrina Carpenter. The 68-year-old also heads into the night as the most-nominated artist, with 11 nods including Video of the Year for “Confessions II – The Film” and Song of the Year for “Bring Your Love,” featuring Sabrina Carpenter. Few artists have made a bigger impact on the VMAs than the “Vogue” singer, who made history at the very first ceremony in 1984. Ahead of her return, we’re revisiting her most memorable ensembles from MTV’s big night. 1984 Getty Images Madonna climbed down a 17-foot tall wedding cake at Radio City Music Hall to perform “Like a Virgin” at the inaugural ceremony. Styled by Maripol, she wore a sheer white lace tulle bustier and skirt, a bridal veil and her scandalizing “Boy Toy” belt. After a lost heel sent her diving, her dress flipped up, and “my manager told me my career was over with,” she told Jimmy Fallon in 2022. Instead, the provocation helped launch her into the pop stratosphere. 1990 Getty Images The night’s most-nominated artist with nine nods for “Vogue”, Madonna performed the hit in 18th-century finery. Her ivory gown came with a corset, hip-widening panniers, ribbons and bows, topped off by a tall blond wig adorned with white feathers. Glenn Close first wore the period costume as the scheming Marquise de Merteuil in the 1988 film “Dangerous Liaisons.” “All of a sudden the idea popped into my head that voguing was not that much different than the court gestures of Marie Antoinette’s court,” choreographer Vincent Paterson, who co-directed Madonna’s Blond Ambition World Tour, told ANALOGr in 2022. 1993 Getty Images Madonna opened the show with “Bye Bye Baby” in a tuxedo with tails, a crisp white shirt, cummerbund and tie, finished with a black top hat. The menswear moment previewed her Girlie Show World Tour, which launched that fall. 1994 FilmMagic The Material Girl ushered in another style era in a pale seafoam Atelier Versace haute couture minidress with a crystal-studded bodice and flouncy skirt, plus silver strappy sandals from the house. Platinum blond finger waves and smoky dark eyes finished the flapper-inspired look. 1995 WireImage Madonna wore Tom Ford-era Gucci: a blue satin shirt unbuttoned over a black bra, with black trousers and a voluminous blowout by Garren. “She [was inspired by] a picture of Catherine Deneuve walking through the lobby with her hair pulled up,” the hairstylist told Page Six Style. 1997 WireImage Madonna dressed for a more somber evening in buttoned-up menswear: a shirt and tie under a black coat, a pencil skirt and a gold pendant necklace. She used her time onstage to honor Princess Diana, who had died that weekend. 1998 Getty Images For her “Shanti/Ashtangi” performance at the 1998 ceremony, Madonna paired a black silk dress with gold jewelry, henna-painted hands and a Vaishnava tilak forehead marking. She later collected her first Video of the Year Moonman in Alexander McQueen: a sequin top and lipstick-red python trousers from his fall 1998 “Joan” collection. 1999 Getty Images Madonna kept it minimalist in a black button-down and trousers from Saint Laurent’s menswear collection by Hedi Slimane. The pared-back look stood in contrast to the drag queens who took the Metropolitan Opera House stage in re-creations of her past video looks. 2003 Getty Images Madonna brought back the wedding cake in 2003 for a twist on her 1984 “Like a Virgin” performance, this time playing the groom to Britney Spears and Christina Aguilera’s brides. She wore a tailcoat and top hat over a black tank with a corseted waist, trousers and mesh arm sleeves. 2018 WireImage Fresh off a 60th birthday trip to Morocco, Madonna wore an Amazigh-inspired ensemble: a spiked silver headpiece, layers of traditional jewelry and a printed robe over a long black dress. 2021 Getty Images for MTV/ViacomCBS Opening MTV’s 40th anniversary show, Madonna shrugged off a Burberry trench to reveal a dominatrix-worthy look: an Atsuko Kudo crop jacket, latex bra and corset, a Moschino leather apron, fishnets and Christian Louboutin pumps. “And they said we wouldn’t last. But we’re still here, motherf–kers,” she told the crowd. Community Guidelines Welcome to the Page Six Community! Our community is about connecting people through open and thoughtful conversations. We want our readers to share their views and exchange ideas in a safe space. In order to do so, we've created a simple set of rules that will improve your experience. Simply put, keep it civil. 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