Celebrity Style

Kendall Jenner Flaunted Her Underboob In A Daring Cutout Dress

And served Old Hollywood glam in the process.

by Sam Ramsden
Kendall Jenner exposed her underboob in a cutout dress.
Emma McIntyre/Getty Images for Academy Museum of Motion Pictures

Kendall Jenner has got the vintage Hollywood aesthetic on lock.

The model and reality star stopped by the fourth annual Academy Museum Gala on Oct. 19, where she rubbed shoulders with the likes of Nicole Kidman, Salma Hayek, and Eva Longoria at the Academy Museum of Motion Pictures in Los Angeles.

Jenner attended the star-studded event with her sisters, Kim Kardashian and Kylie Jenner, both of whom arrived wearing vintage Mugler. Kendall, however, went with another designer — and her Gala look was one of the most daring of the night.

Kendall’s Cut-Out Couture

Posing on the red carpet, Kendall stunned in an all-black, floor-length Schiaparelli Spring 2024 couture dress, featuring a cut-out design around the cleavage region that put her underboob on full display.

Kendall Jenner at the Academy Museum of Motion Pictures 4th Annual Gala. Stefanie Keenan/Getty Images for Academy Museum of Motion Pictures

Complementing her daring black gown, the model wore a pair of black Schiaparelli Bijoux Mules S heels, and showed off her blonde locks that channeled Marylin Monroe’s iconic ‘do.

Kendall’s Daring PFW Look

This isn’t the first time The Kardashians star has reached for a boundary-pushing ‘fit as of late. On Sept. 23, Kendall strutted down the runway at the Le Défilé: Walk Your Worth Spring/Summer 2025 show for L'Oréal Paris wearing a spicy see-through red gown.

Stephane Cardinale - Corbis/Corbis Entertainment/Getty Images

The floor-length, Jessica Rabbit-style dress was designed with see-through mesh corset detail, elegant attached gloves, and a high turtleneck neckline. However, the pièce de résistance of Kendall’s Paris Fashion Week gown was the massive cut-out across the chest that left half of her matching red bra completely exposed.