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.