Worst Kentucky Derby Fashion Now & Then

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

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

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

Ashanti
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Singer Ashanti went overboard with the floral print in 2006.

Johnny Weir & Tara Lipinski
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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
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This television actress failed to bring her A-game to the Derby in 2007.

Tori Spelling
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Tori Spelling’s Derby fashion fizzled in 2005.

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