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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, without them the Academy Awards would be a sea of forgettable gowns.

From Jennifer Lawrence to Jennifer Lopez, 2000 to 2019, these were the boldest looks on Hollywood's most beloved red carpet. Take a glance, which gowns are forever stamped in your memory?