From Jennifer Lopez’s iconic sheer Versace dress in 2000 to Britney Spears’ angelic Y2K look that same year, here are all the most audacious ensembles to have ever graced the Grammys red carpet.

Often cited as one of the most iconic dresses in the history of the Oscars, this belted white floral dress - worn by Audrey Hepburn when she scooped the award for best actress for Roman Holiday ...

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The daring dress was divisive and cemented her spot in the world of fashion discourse. She then attended her first Met Gala this year and was said to have been styled in part by Anna Wintour herself.

Backless tops, see-through dresses, and neon outfits have all had their moment in the spotlight. Here's a look at those styles and some of the other boldest pieces ever worn at the prestigious event.

For performances, the singer often wears sparkly rompers and sheer dresses ... Swift wore one of her most daring looks ever at the 2016 Vanity Fair Oscars after-party. Taylor Swift at the 2016 ...

Backless tops, see-through dresses, and neon outfits have all had their moment in the spotlight. Here's a look at those styles and some of the other boldest pieces ever worn at the prestigious ...