Same Dress, 30-Year Gap: Who Wore It Better, Kendall Jenner or Cindy Crawford?

Kendall Jenner gave a major nod to supermodel history at a Giorgio Armani event in Milan last night. The model attended the party celebrating the brand’s Power of You fragrance wearing a vintage gown that Cindy Crawford had first worn at a gala in 1999.

The sparkling ’90s Armani dress hugged Jenner’s figure perfectly. It was covered in silver sequins with sheer mesh details, showing that the design has timeless appeal. Jenner paired the look with square-toed heels, while Crawford had originally worn delicate metallic sandals, showing a small but stylish difference between the two interpretations of the same dress.

Jenner and Crawford’s styling choices were otherwise very similar. Both went with voluminous ’90s-inspired hair, glowing skin, and minimal jewelry that allowed the gown to shine.

um luxo esse vestido pic.twitter.com/dPSXnWdtcw

— ѵic (@kendolsz) February 27, 2026

How the dress moved from one generation of supermodels to the next isn’t completely clear. Jenner and Crawford have met at events before, like the 2016 Met Gala, but it’s more likely Jenner got the gown from her family’s fashion archive. The Kardashian-Jenner archive, Kardashian Kloset, shared the dress on Instagram in 2024, highlighting the family’s access to iconic vintage pieces.

This moment in Milan reminded fans of the lasting influence of supermodel style. As Jenner wore the gown decades after Crawford, it was clear that a great dress doesn’t lose its power over time.

Kendall brought the dress to life in a way that honors Crawford while making it her own. Who do you think wore it better—Crawford or Jenner? Share your thoughts in the comments.