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Kentucky Derby's Most Memorable Fashion Moments Over the Years

28 photos
May 03, 2025 3:18 AM
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Kentucky Derby Fashion, Lauren Conrad
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Mike Coppola/Getty Images for Moet & Chandon

Lauren Conrad

We're coming clean and noting the Laguna Beach alum stunned in a perfectly coordinated beige ensemble—hat and all—at the 2013 derby.


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Jeff Gentner/Getty Images

Kim Kardashian

No one can object to how great the lawyer-to-be looked in black and white at the 2009 Kentucky Derby. 


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Michael Loccisano/Getty Images for Churchill Downs

Richard Lawson & Tina Knowles

The now-exes coordinated in black and white ensembles for the 2018 event.


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AP Photo/Darron Cummings

Jessica Simpson

The singer's pink hat and floral dress for the 2004 Kentucky Derby were so good they may just take your breath away.


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