The Kentucky Derby vs. the Royal Wedding

Which event boasts crazier hats?

The outfit that real estate agent Cora Jacobs wore to the 1971 Kentucky Derby was so outlandish that it earned a mention in the Louisville Courier-Journal: “She made hot pants absolutely de rigueur for the day,” the paper gushed. “She showed up at the clubhouse garden in very brief, white shorts topped by a flesh colored shell overlaid in red silk covered with rose petals. Her hat, and she always wears an outstanding one, was made of white ostrich feathers and ‘hundreds’ of red organza roses.”

Chris Goodlett, curator of collections at the Kentucky Derby Museum, credits Jacobs as the instigator of the derby’s outlandish hat tradition. Her 1974 hat, pictured below, at center, is now on display in the museum, along with her white dress inscribed with the 99 names of past derby winners.

Less-psychedelic hats had been fixture of horse races long before the first competition at Churchill Downs in 1875. Southerners originally wore wide-brimmed straw hats to save their necks from the smoldering sun (women in particular prized fair skin). But for the festive race-day look, they took their style cues from the Brits, who first infused a sense of fashion into the historic Epsom Derby, dating back to the 1600s.

So which country boasts the most garish headwear? We’ve pitted hat against hat and in a slide show of each event’s most ostentatious headwear. Click here to view the slide show and decide for yourself who should win the hats race.