You can't have a look back at daring fashion without including Nicole Kidman's John Galliano for Dior dress worn to the 1997 Ceremony. Chartreuse, mink-trimmed, and silk, it has gone down in style history as one of the bests.
Jennifer Lopez is known a very specific style of gowns: nude-colored, plenty of sparkle, and even more skin. But at the 2003 Academy Awards, the singer went for a romantic, one-shouldered gown in an unexpected mint hue that was a welcome change.
As the off-screen counterpart to Carrie Bradshaw, Sarah Jessica Parker can always be counted on for a daring fashion moment. This Chanel Couture gown from the 2010 ceremony was equal parts elegant and unexpected.
She's Cate the Great for a reason. Blanchett made a major statement in a lilac-hued Givenchy Couture gown with tonal embellishments at the 2011 Academy Awards.
From the front, Hilary Swank was completely covered up, but when she turned around, that was the "Wow" moment. This Guy LaRoche dress was an instant classic.
It's an outdated rule that redheads shouldn't wear red--and one that clearly Amy Adams isn't listening to. The actress accessorized the bold hue with a major statement necklace at the 2009 awards.
Beaded bodice, ombre purple, a full train: Zoe Saldana's Givenchy couture dress certainly had a lot going on, but on the actress, it all worked in perfect harmony.
It's not often you see a formal Peter Pan collar, but when it's Chanel couture, that's a different story. Kirsten Dunst was just the girl to pull off the bold neckline.
Before cape gowns came with every red carpet, Gwyneth Paltrow kicked off the trend in a simple, masterfully crafted Tom Ford number at the 2012 ceremony.
It was the leg that launched 1,000 memes. Angelina Jolie made quite the statement in 2012 awards; a look that many others have since tried to emulate to less effect.
If you are to believe stylist lore, Anne Hathaway's Prada gown was a decision made just moments before hitting the carpet. True or not, it made for a refreshingly simple look.
Naomi Watts tried out a new silhouette altogether in a fashion-forward take on the bandeau. It was a sparkling addition to the 2015 carpet.
Rachel McAdams opted for a lesser-known designer, August Getty Atelier--a bold red carpet mood in itself--for the 2016 awards, wearing a slinky, jade number.
The Academy Awards typically calls for strict black tie, but newcomer Daisy Ridley made a memorable showing in tea-length Chanel couture.
A bubble-hem is not one typically seen on the red carpet, but Alicia Vikander made it work--it was custom Louis Vuitton, after-all--in 2016.