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 26 of 56 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 26 A woman was seen in the grandstands wearing a hat prior to the 136th running of the Kentucky Derby on May 1, 2010. Previous Next Start Slideshow WomenKentucky DerbyHistory