The Oscars aren’t just the most prestigious awarding ceremony in acting history. It is also that one annual event where some of the biggest stars in the entertainment industry come dressed to the nines, captivating viewers and critics with exquisite designer pieces and jaw-dropping outfits. We’ve curated some of the looks that will go down as some of the most unforgettable outfits in Oscar history—either for their timelessness or being fashion faux pas.
Kendall Jenner
Kendall Jenner is easily a red carpet favorite. Much like how her family rarely makes mistakes in terms of money management, rarely does the supermodel ever make the mistake of donning a fashion no-no. While she may not have graced the red carpet for the Academy Awards itself, she is a staple figure at the after-parties, particularly the one hosted by Vanity Fair.
This member of the Kardashian-Jenner brood is not one to shy away from sexy dresses that show a lot of skin and accentuate her assets, and she made a bold move when she wore a risqué Rami Kadi dress during the Vanity Fair Oscars after-party in 2019.