Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

Madonna serves up a sultry menswear moment in bustier at 2026 MTV VMAs

Madonna’s 5 boldest VMAs looks: From 1984 to her 2026 return
Madonna’s 5 boldest VMAs looks: From 1984 to her 2026 return

Madonna brought her signature edge to the 2026 MTV VMAs, putting a sultry spin on menswear with a bustier display.

The Queen of Pop brought a sultry edge to menswear as she opened the awards ceremony, pairing an oversized black blazer with a bold bustier, high-waisted shorts and thigh-high boots for her star-studded performance.

Madonna layered a belted, long-sleeve blazer over a red bustier, which peeked through the open front.

She completed the look with statement black boots while performing a medley of songs from her latest album, Confessions II.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

Madonna made her long-awaited VMAs performance comeback in 2026, taking the stage live at the awards ceremony for the first time in 23 years.

Sabrina Carpenter joined Madonna for Bring Your Love, followed by Charli xcx for the debut of their Danceteria Afterhours remix.

6 Madonna’s most iconic VMAs looks

Madonna descended a 17-foot wedding cake at Radio City Music Hall to perform Like a Virgin at the inaugural VMAs in 1988, wearing a sheer lace bustier, skirt, bridal veil and Boy Toy belt.

Instead, the moment helped propel her to pop superstardom.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

In 1990, Madonna, the hit in an ivory 18th-century gown featuring a corset, panniers, ribbons and bows, topped with a feathered blond wig.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

For the VMA, 1993, 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.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

In 1995, the Popular singer turned heads as she wore Tom Ford-era Gucci: a blue satin shirt unbuttoned over a black bra, with black trousers and a voluminous blowout by Garren.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return

Madonna revived her iconic wedding-cake set in 2003, putting a new spin on her 1984 “Like a Virgin” performance as she played the groom to Britney Spears and Christina Aguilera’s brides.

She wore a tailcoat and top hat over a corseted black tank, trousers and mesh sleeves.


Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return


Kicking off MTV’s 40th anniversary celebration in 2021, Madonna slipped off her Burberry trench to unveil a daring look comprising an Atsuko Kudo crop jacket, latex bra and corset, Moschino leather apron, fishnets and Christian Louboutin pumps.

Madonna’s 6 boldest VMAs looks: From 1984 to her 2026 return