Kendall Jenner's Best Red Carpet Looks Through the Years

Kendall Jenner may have enviable street style, but it's her epic red carpet looks that launched a thousand naked dresses. The model has in recent years championed sheer illusion, bare bums, and nearly naked tops everywhere from the Oscars to the Met Gala, but has also shown a more whimsical side, occasionally turning to voluminous dresses, tulle-filled looks, and even feathered frocks. Plunging necklines, open backs, and plenty of crystals have been on Jenner's fashion menu, which has only gotten more confident and focused with time.

The supermodel, who has admitted in the past that she's "more introverted" than her Kardashian sisters, who she said "are much louder," has certainly found her voice on the red carpet, regularly communicating through her looks that she's more than comfortable showing some skin. When her first high fashion runway show for Marc Jacobs in 2014 ended up involving a completely sheer top, the 818 Spirits founder certainly kept her cool, recalling to Vogue, "I was pretty chill, even though my boobies were out."

With her quiet confidence leading the way, Jenner has become a standout on some of the hardest to conquer red carpets, namely the Met Gala and the Oscars after-party, where one 2019 look won the night (and nearly broke the internet). Jenner's willingness to push the limits for fashion shows no signs of wavering. While discussing her longtime partnership with Calvin Klein, the Keeping Up with the Kardashians star was asked by Elle in 2023 if there were any new trends she would be willing to try out. Her cool-as-a-cucumber response? "I am always willing to take a risk."

Keep scrolling for a few of Kendall Jenner's best red carpet looks to date.