Popsugar Love Women Why Do Women Wear Hats at Kentucky Derby? Why Women Wear Fancy Hats at the Kentucky Derby April 30, 2015 by Annie Gabillet View On One Page Photo 31 of 56 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 31 Do you recognize Jessica Simpson underneath the pink brim at the Derby in 2004? Previous Next Start Slideshow WomenKentucky DerbyHistory