Madonna's Most Iconic VMA Looks: A Fashion Retrospective
As the pop icon prepares to open the 2026 VMAs, revisit her most memorable fashion moments from the awards show.
Madonna is set to make her return to the MTV Video Music Awards stage to open the 2026 ceremony on Sunday, Sept. 27. This performance marks her first appearance at the VMAs in 23 years. The Queen of Pop is also the most-nominated artist heading into the event, with 11 nods.
Madonna's impact on the VMAs is undeniable, with her fashion choices often as memorable as her performances. She has been a fixture at the awards show since its inception in 1984, consistently pushing boundaries and setting trends.
Early Years: Shock and Style
In 1984, Madonna made history at the inaugural VMAs by descending from a wedding cake to perform "Like a Virgin." Styled by Maripol, she wore a daring white lace bustier and skirt, complete with a bridal veil and her signature "Boy Toy" belt. A wardrobe malfunction, where her heel came off and caused her dress to flip up, became an iconic moment that Madonna later recalled as nearly ending her career, though it ultimately propelled her to superstardom.
Her 1990 performance of "Vogue" saw her embrace 18th-century grandeur. Dressed in an elaborate ivory gown with panniers and a towering wig adorned with feathers, she channeled Marie Antoinette. Choreographer Vincent Paterson noted that the historical gestures of the era inspired the voguing performance.
Shifting Styles: Menswear and Glamour
Madonna's fashion evolved through the 1990s. In 1993, she opened the show with "Bye Bye Baby" in a sharp tuxedo with tails, a crisp white shirt, and a top hat, previewing her "Girlie Show" World Tour. The following year, she opted for a pale seafoam Atelier Versace haute couture minidress with a crystal-studded bodice, paired with finger waves and dark eyes, evoking a flapper-inspired look.
In 1995, she wore a daringly unbuttoned blue satin shirt from Tom Ford-era Gucci over a black bra, paired with trousers. Her hairstyle, a voluminous blowout, was inspired by Catherine Deneuve. A year later, in 1997, she adopted a more somber look with a black suit, shirt, and tie, honoring Princess Diana. For her "Shanti/Ashtangi" performance in 1998, she incorporated traditional Indian elements with a silk dress and henna-painted hands before later accepting a Video of the Year award in Alexander McQueen.
Reinvention and Bold Statements
The late 90s saw Madonna continue to experiment. In 1999, she sported a minimalist black button-down and trousers from Saint Laurent's menswear collection, a stark contrast to the drag queens on stage reinterpreting her past looks. In 2003, she recreated her iconic "Like a Virgin" performance, this time as a groom, famously kissing Britney Spears and Christina Aguilera, who were dressed as brides. Madonna wore a tailcoat and top hat for the provocative moment.
More recent appearances have also made a splash. In 2018, inspired by a trip to Morocco, she wore an Amazigh-inspired ensemble featuring a spiked silver headpiece and traditional jewelry. At the 2021 VMAs, Madonna opened the show in a dramatic Atsuko Kudo outfit, revealing a black leather corset, apron, and fishnets beneath a Burberry trench coat, declaring, "And they said we wouldn’t last. But we’re still here, motherf–kers."
