Madonna is gearing up for another headline-making performance at the VMAs.
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The iconic pop star is set to kick off the 2026 VMAs on Sunday, September 27, marking her first appearance on the VMA stage in 23 years. She’s expected to be accompanied by “special guests,” with rumors swirling about appearances from Charli XCX and Sabrina Carpenter.
At 68, Madonna leads the pack as the evening’s top nominee, securing 11 nominations. Her nominations include Video of the Year for “Confessions II – The Film” and Song of the Year for her track “Bring Your Love,” which features Sabrina Carpenter.
Madonna has left an indelible mark on the VMAs over the years, starting with her groundbreaking performance at the first-ever ceremony in 1984. As she prepares for her upcoming performance, let’s take a look back at some of her most unforgettable VMA outfits.
1984
Madonna made a sensational debut at the very first VMAs, descending from a 17-foot wedding cake at Radio City Music Hall to perform “Like a Virgin.” Her outfit, designed by Maripol, featured a sheer white lace tulle bustier and skirt, complete with a bridal veil and a controversial “Boy Toy” belt. A mishap that caused her heel to come off led to an unintended reveal, but rather than ending her career, Madonna told Jimmy Fallon in 2022 that it catapulted her to stardom.
1990
At the VMAs where she was the most nominated artist with nine nominations for “Vogue,” Madonna performed dressed in 18th-century attire. She wore an ivory gown with a corset and elaborate panniers, adorned with ribbons and bows, and a towering blond wig decorated with white feathers. The costume was previously worn by Glenn Close in the 1988 movie “Dangerous Liaisons.” Madonna’s choreographer for the Blond Ambition World Tour, Vincent Paterson, explained to ANALOGr in 2022 that the concept of voguing reminded him of the court gestures from Marie Antoinette’s era.
1993
Opening the show, Madonna performed “Bye Bye Baby” in a tuxedo complete with tails, a crisp white shirt, cummerbund, and tie, topped with a black top hat. This menswear-inspired look previewed her Girlie Show World Tour that started later that year.
1994
Madonna introduced a new style phase in a pale seafoam Atelier Versace haute couture minidress with a crystal-studded bodice and a flouncy skirt, complemented by silver strappy sandals. Her look was completed with platinum blond finger waves and dark smoky eyes, channeling a flapper vibe.
1995
Dressed in a Tom Ford-era Gucci ensemble, Madonna wore a blue satin shirt left open over a black bra, paired with black trousers. Her hairstyle, a voluminous blowout by Garren, was inspired by a photo of Catherine Deneuve, as the hairstylist revealed to Page Six Style.
1997
For a more subdued appearance, Madonna opted for a conservative menswear look: a shirt and tie under a black coat, paired with a pencil skirt and a gold pendant necklace. She used her moment on stage to pay tribute to Princess Diana, who had passed away that weekend.
1998
Performing “Shanti/Ashtangi” at the 1998 ceremony, Madonna dressed in a black silk gown accessorized with gold jewelry and henna-painted hands, also sporting a Vaishnava tilak on her forehead. Later that evening, she accepted her first Video of the Year award in an Alexander McQueen outfit featuring a sequin top and lipstick-red python trousers from his fall 1998 “Joan” collection.
1999
Madonna chose a minimalist look with a black button-down and trousers from Saint Laurent’s menswear line by Hedi Slimane. Her simple style contrasted sharply with the drag queens who shared the stage, dressed in iconic looks from her past videos.
2003
In a nod to her iconic 1984 performance, Madonna revisited the wedding cake theme in 2003, this time playing the groom to Britney Spears and Christina Aguilera’s brides. Her outfit consisted of a tailcoat and top hat, paired with a black tank featuring a corseted waist, trousers, and mesh arm sleeves.
2018
Celebrating her 60th birthday with a trip to Morocco, Madonna embraced the local Amazigh culture in her outfit: a spiked silver headpiece, layers of traditional jewelry, and a printed robe over a long black dress.
2021
At MTV’s 40th anniversary event, Madonna shed a Burberry trench coat to unveil a bold dominatrix-inspired ensemble. She wore an Atsuko Kudo crop jacket, a latex bra and corset, a Moschino leather apron, fishnets, and Christian Louboutin pumps. Addressing the audience, she proclaimed, “And they said we wouldn’t last. But we’re still here, motherf–kers.”
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Ellis McDowell is a trend analyst with a sharp eye for spotting the next big thing in entertainment. With years of experience in digital media and trend forecasting, Nora tracks the movements of influencers, viral content, and entertainment trends. Her insights help shape the stories that captivate our audience.
