Cindy Crawford, 1992
As the host of MTV’s House of Style, fans knew supermodel Cindy Crawford would bring her fashion A-game to the red carpet of the 1992 VMAs. Wearing a leather and lace bustier with plenty of straps and buckles, her look was pretty daring.
Getty Images Photo by Ron Galella, Ltd.
The strappy gown was part of Versace’s risqué collection aptly called Miss S&M. Short of bringing a whip to the red carpet, Cindy let her head-turning dress do the talking. The look was even worn by singer Dua Lipa at the 2022 Grammy Awards.
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Sinéad O'Connor, 1990
In 1990, Sinéad took home three MTV Music Video Awards, including Video of the Year, Best Female Video, and Best Postmodern Video for "Nothing Compares 2 U." Her signature defiance was in full play during the performance. She performed in a loose-fitting white maxi dress, teasingly revealing her sexy black slip underneath. Well, if they wanted a skin show, she would do it on her terms!
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The singer completed the look with oval sunglasses and Doc Martens. Few artists have rocked the boat like Sinead O’Connor, who defied tropes of what artists “should” be.