Kendall Jenner Styles Cindy Crawford's Circa-1999 Armani Dress for Milan Fashion Week
Rumor has it, it belonged to Jenner's mom or sister at one point.
Who else was shocked to see Kendall Jenner traded Emporio Armani's runway for the Fall 2026 front row? The surprises continued after the February 26 Milan Fashion Week show, too. She arrived at Emporio Armani's "Power of Fragrance" party in Cindy Crawford's vintage Armani dress. The lore gets even deeper: It may have been straight from her family's closet.
Not only did the global fragrance ambassador (likely) smell of vanilla, passionfruit, and orange, she oozed cool-girl glamour in skintight silver. Stylist Dani Michelle used Jenner's ambassadorship to access the label's '90s archives, though the exact date her spaghetti-strap slip debuted remains a mystery.
Each feature—especially the scoop neck and ankle-grazing skirt—fit her like a glove. Sequins sculpted into asymmetrical, horizontal stripes decorated every square inch of the dress. The motif matched the shine and shape of chainmail. Even Jenner's square-toe kitten heels got the metallic silver memo.
Kendall Jenner was all smiles at Milan Fashion Week in a decades-old, silver Armani dress.
According to Kardashian Kloset on Instagram, the "rare" Giorgio Armani gown originally belonged to a Kardashian. It's unclear whether Kim or Kris Jenner was the proud owner, though. The family's authentic luxury retail site listed the exact chainmail-esque maxi in Nov. 2024, alongside vintage Alaïa, Chanel, Calvin Klein, Versace, and more. Who scored the silver look? The world may never know. All that matters is it ended up in Jenner's hands, a moment her momager would be undeniably proud of.
The ties to major names don't stop there. Cindy Crawford wore the aforementioned midi nearly three decades ago. On March 4, 1999, she—and her Armani design—sparkled at a St. Jude Children's Hospital benefit. The supermodel styled it somewhat similarly to her It-girl successor: with matching peep-toe mules, blink-and-you'll-miss-them jewelry, and a classic '90s blowout.
Usually Kaia Gerber gets first dibs on her mom's archival dresses, but Jenner and Crawford walked the 2016 Met Gala stairs together. So she certainly has an in with the icon.
Almost 30 years ago, Cindy Crawford wore the same sequin dress at a Hollywood benefit.
If you haven't gathered by now, it's against Jenner's M.O. to walk a red carpet in an average designer dress. Milan Fashion Week requires something much more notable: better yet, a piece with major fashion history. Since her red carpet walks are so few and far between, she makes each one a moment. Jenner hasn't secured an official look this archival since her circa-1992 Mugler gown at the 2025 Vanity Fair Oscars Party. Let's hope she keeps this up at the 2026 Oscars.
