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Worst Kentucky Derby Fashion Now & Then


Source: Getty Images

Break out your huge, over-the-top hat and pour yourself a mint julep while you check out some of the wildest and worst Kentucky Derby style moments to take place at Churchill Downs.

Miranda Lambert
Source: Stephen Lovekin/Getty Images

Country singer Miranda Lambert missed the boat with her flesh-colored ensemble.

Kate Gosselin
Source: Getty Images

Reality star Kate Gosselin got feather’s ruffled in 2012 with her hat choice.

Debra Messing
Source: Michael Loccisano/Getty Images

Television star Debra Messing dropped the ball with this neutral number in 2012.

Ashanti
Source: Getty Images

Singer Ashanti went overboard with the floral print in 2006.

Johnny Weir & Tara Lipinski
Source: Neilson Barnard/Getty Images

This ice skating pair went big with the Kentucky Derby theme in 2015, Weir sporting a head piece adorned with dozens of roses.

Melissa Joan Hart
Source: Getty Images

This television actress failed to bring her A-game to the Derby in 2007.

Tori Spelling
Source: Peter Kramer/Getty Images

Tori Spelling’s Derby fashion fizzled in 2005.

Joey Fatone
Source: Getty Images/Michael Loccisano

Singer and actor Joey Fatone wore an outfit fit more for the circus with his bold red jacket and bow tie at the 2012 Derby event.

Bethenny Frankel
Source: Jeff Gentner/Getty Images

Real Housewives reality star sported this bubble gum pink number in 2009.

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