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 53 of 56 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 53 It was a go big or go home hat for this woman in 2014. Previous Next Start Slideshow WomenKentucky DerbyHistory