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 37 of 56 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 37 At the 2012 race, a woman wore a pretty cream and red polka-dot hat. Previous Next Start Slideshow WomenKentucky DerbyHistory