Kendall Jenner Has a Supermodel Moment in Cindy Crawford’s 1999 Dress

Kaia Gerber tends to have the most direct line to her mom Cindy Crawford’s vintage archive. Over the years, the model-turned-actor has frequently dipped into Crawford’s closet for red carpets and galas alike, wearing her archival Hervé Leger and Calvin Klein pieces. But in Milan last night, it was Kendall Jenner who had special access to the super’s iconic wardrobe.

At a Giorgio Armani party celebrating its Power of You fragrance, Jenner traded her minimal Italian style for full-on sparkle. She wore a vintage ’90s Armani gown that Crawford had debuted at a 1999 gala. The design fit Jenner like a glove, curving around her figure with silver sequins interlaced with sheer mesh.

Jenner and Crawford actually styled their ensembles in strikingly similar fashion, each opting for bouncy ’90s blowouts, luminous skin, and a restrained approach to jewelry that let the dress take center stage. The one notable point of departure came at the ground level: Crawford finished the look with delicate metallic sandals, while Jenner grounded hers with square-toed heels.

As for how the item made its way from one generation of American supermodel to the other remains unclear. Jenner and Crawford have crossed paths socially and professionally in the past, most notably at the 2016 Met Gala, where they posed for photos on the museum steps. (Jenner and Gerber are also close.) More likely, Jenner secured the piece through her family’s extensive fashion archive—the gown was shared in 2024 on the Instagram of the Kardashian-Jenners’ fashion archive, Kardashian Kloset.

However it came into Jenner’s possession, the moment underscored the allure of true supermodel style.