Decades Apart, One Iconic Dress: Kendall Jenner vs. Cindy Crawford – Who Wore It Best?

Kendall Jenner turned heads in Milan last night, wearing a vintage gown that Cindy Crawford first wore back in 1999. The dress, a ’90s Armani design covered in silver sequins with sheer mesh details, fit Jenner perfectly, showing that the style still holds up decades later.

Jenner styled the gown with square-toed heels, while Crawford had originally paired it with delicate metallic sandals. Both models kept their accessories simple and their hair in voluminous ’90s-style blowouts, letting the dress take center stage. The similarities highlighted the timeless appeal of the design, while the small differences added a modern twist.

It isn’t completely clear how Jenner got access to the iconic dress. She and Crawford have met at events before, including the 2016 Met Gala, but it seems more likely that Jenner borrowed it from her family’s fashion archive. The Kardashian-Jenner archive, Kardashian Kloset, had previously shared the gown on Instagram in 2024.

um luxo esse vestido pic.twitter.com/dPSXnWdtcw

— ѵic (@kendolsz) February 27, 2026

This event showcased how classic supermodel fashion can be passed from one generation to the next. Jenner honored the original look while making it her own, proving that a great gown never goes out of style.

Kendall brought new life to Crawford’s iconic dress while respecting its original glamour. Who do you think wore it better, Crawford or Jenner? Share your opinion in the comments.