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MTV VMAs: Riskiest Fashion Moments of All-Time

32 photos
Sep 06, 2025 9:00 AM
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Rose McGowan, MTV Video Music Awards, Worst Dressed
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Jeffrey Mayer/WireImage.com

Rose McGowan

Before Rihanna hit the CFDA Awards in 2014, there was the Charmed actress at the 1998 MTV VMAs in this see-through number. 


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Axelle/Bauer-Griffin via Getty Images

Rita Ora

She never lets us down! Arriving on the red carpet in 2018, the singer left little to the imagination with this sheer gown.


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Axelle/Bauer-Griffin via Getty Images

Bella Hadid

The supermodel left the typical dress at home, and instead, opted for something fun, flirty and fierce in 2019.


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Kevin Mazur/WireImage.com

Macy Gray

Back in 2001, Instagram wasn't yet a thing, so Macy took it upon herself to throw in some shameless self-promotion.


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Jason Merritt/Getty Images

Jessie J

We applaud the singer's determination to not let her injury get in the way of a fabulous outfit in 2011.


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Getty Images

Amber Rose & Blac Chyna

Twins! Leave it to stars to make a serious statement on the 2015 red carpet. 


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Jamie McCarthy/Getty Images

Farrah Abraham

In 2016, the Teen Mom alum went full Wonder Woman—literally.


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Jim Spellman/WireImage

Mariah Carey

The "Fantasy" singer brought... well, the fantasy to the red carpet in 1997. Although her black co-ord set was simple, it was oh-so-striking.


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