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 2 of 56 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 2 Spectators made their way into the races in 1995. Previous Next Start Slideshow WomenKentucky DerbyHistory