The MTV Video Music Awards have never exactly been known for playing it safe. While other awards shows tend to favor polished gowns and predictable glamor, the VMAs have always been the place where celebrities get to have a little fun. Back in the day, it’s where Jennifer Lopez would show up in white jeans and a matching bandana, and where Lady Gaga would gag us with an ensemble more shocking than the last. The performances may be legendary, but the fashion moments are often just as unforgettable. Year after year, the VMAs have delivered the kind of red-carpet looks that spark headlines, inspire Halloween costumes, and become permanently etched into pop-culture history. From daring silhouettes to downright unexpected styling choices, these are the outfits that helped define the spirit of the VMAs.
The VMAs return on Sunday (Sept 27) and we can’t wait to see what the stars have in store. But throughout history, there are the looks that need no introduction, like Destiny’s Child bringing coordinated girl-group glamor to the ceremony, creating a visual time capsule of late-’90s and early-2000s style that feels instantly nostalgic and still relevant today. Over the years, the red carpet has given us barely-there looks, questionable accessories, major fashion risks, and outfits so memorable they practically became pop-culture landmarks. And some of the onstage looks have been just as quintessential (think less Britney Spears with the snake and more Britney in the rhinestone catsuit that sparked a thousand puritan complaints).
The most iconic moments belong to the women who understood the assignment long before “viral fashion moment” was a thing. From jaw-dropping gowns to boundary-pushing ensembles, these moments capture what makes VMA fashion so uniquely entertaining: There are no rules, and the bigger the statement, the better. Here are 10 of the most iconic looks to ever hit the MTV VMAs.
Lady Gaga, 2010
Lady Gaga’s 2010 meat dress wasn’t just a red-carpet look — it was a full-blown pop-culture moment, turning one of the VMAs’ most outrageous outfits into one of the most instantly recognizable fashion statements of the decade.
Madonna, 1984
Madonna’s 1984 bridal VMAs outfit is the blueprint for the kind of fashion moment the show would become famous for. Climbing onto the stage for “Like A Virgin” in a white lace bustier, tutu, layered jewelry, and “Boy Toy” belt, she turned bridal dressing on its head and made an instantly recognizable pop-culture statement.
Destiny’s Child, 2000
At the 2000 VMAs, Destiny’s Child leaned all the way into coordinated Y2K glamour, serving up colorful, curve-hugging looks that perfectly captured the maximalist spirit of the era — and cemented their place in VMA fashion history.
Sabrina Carpenter, 2025
As VMA fashion has gradually traded some of its anything-goes chaos for safer, more polished red-carpet dressing, Sabrina Carpenter’s 2025 look proved that a little old-school glamor can still make an impact. The retro-inspired ensemble was polished and playful without feeling predictable — a reminder that you don’t need a headline-grabbing gimmick to deliver a memorable VMA fashion moment.
Lil Kim, 1999
Lil’ Kim’s 1999 VMAs look remains one of the most daring red-carpet moments in pop culture history. The purple one-shoulder jumpsuit, complete with a strategically placed pastie and matching wig, was unapologetically revealing, gloriously campy, and so unmistakably Lil’ Kim that it instantly became a fashion moment. And led to an iconic on-stage moment with Diana Ross jiggling Lil Kim’s breast that is etched into our memories forever.
Miley Cyrus, 2015
By 2015, Miley Cyrus was firmly in her rebellious era, and her VMA look was every bit as unapologetic as the persona she had embraced. The futuristic, barely-there ensemble — paired with sky-high platforms and a playful space-age vibe — captured the anything-goes spirit of her style at the time and made sure she arrived ready to steal the spotlight.
Cher, 2010
Cher’s 2010 VMAs look felt like a full-circle fashion moment — and an especially poignant one now following the death of her longtime collaborator Bob Mackie. Wearing a look reminiscent of the sheer, skin-baring glamor of her iconic ’80s look, one of Mackie’s signature creations, she proved that the visual language the pair created together still had plenty of staying power decades later.
Rihanna, 2016
Rihanna’s 2016 VMAs look proved that an onstage outfit can be just as memorable as a red-carpet one. Performing in a casual-chic ensemble topped with feathered bralet and a mesh durag, she made the accessories feel like the centerpieces rather than an afterthought, effortlessly channeling the cool, Black as hell, streetwear-meets-pop-star sensibility that has long defined her style.
Britney Spears, 2000
Before the snake, there was Britney Spears’ 2000 VMAs look: a barely-there, Swarovski-crystal-covered bodysuit that left very little to the imagination. The sheer, sparkling ensemble was considered shockingly revealing at the time, but it also captured Britney at the height of her pop-star ascent — turning controversy into one of the most talked-about fashion moments of the night.
Jennifer Lopez, 2000
Jennifer Lopez arrived at the 2000 VMAs in a look that was pure early-aughts J.Lo: a white Sean John tracksuit, crop top, white bedazzled bandana, and plenty of swagger. The coordinated streetwear moment captured the era’s hip-hop-meets-Hollywood glamor (her date was a man we no longer acknowledge), while the casual-meets-sexy styling became, once again, an instantly recognizable snapshot of peak Y2K fashion.
The 2026 MTV VMAs will air Sunday, September 27that 7:30pm ET/ 4:30pm PT on CBS, MTV and Paramount+
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