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Every award show is an opportunity for an actress to have a memorable fashion moment, be it iconic or infamous (no pressure!). Here at Livingly, we like to celebrate adventurous style and ladies who take a gamble, whatever the outcome.

So whether you considered them the best dressed or the worst dressed, these celebs took major sartorial risks on fashion's biggest night. And thank goodness, because without them the Academy Awards would be a sea of forgettable gowns.

From Jennifer Lawrence's dramatic Dior Couture dress (which she memorably took a tumble in) to Halle Berry's sheer Elie Saab number and Angelina Jolie's leg-baring Atelier Versace, these are the boldest looks ever worn on Hollywood's most beloved red carpet. And if you thought only award show icons like these three are capable of standing out at the Oscars, you'll be surprised at the head-turning looks newcomers have worn to the event. Who could ever forget the voluminous hot-pink Valentino gown Gemma Chan sported at her very first Academy Awards in 2019, or Janelle Monae's elaborate Elie Saab look from 2017?

Keep scrolling to see the biggest risk takers on the Oscars red carpet through the years. Which gowns are forever stamped in your memory?