History and High Heels: The Kentucky Derby

The Kentucky Derby is a famous annual event held at the Churchill Downs in Louisville, Kentucky that features a grade 1 Thoroughbred race on the first Saturday in May. The event was founded by Meriwether Lewis Clark, Jr., grandson of the famous William Clark from the Lewis & Clark Expedition, after he had visited both London and Paris horse races during the 1860s. In 1875 the first race was ran between 15 three-year old Thoroughbreds and in front of nearly 10,000 spectators. The race holds several traditions, including the famous Mint Julep cocktail that is the race staple drink. The Kentucky Derby is often referred to as The Run for the Roses due to the time-honored practice of presenting the winner with a blanket of 554 roses.

Flappers study the racing program in the Churchill Downs paddock circa 1926.
courtesy of Kentucky Derby Archives

One more famous aspect of the race is the tradition of women to dress in a fairly conservative, classic style with outrageous hats atop their heads. This has been going on for years and one can see in the old 1920s spectator photos the women all wearing the stylish narrow wool hats so indicative of that era (seen above). When glancing through the pictures, the hats have become exceedingly ostentatious over the past couple decades. The tall plumes of feathers and banded caps have also become popular recently largely due to the fashion inspiration we all found in Kate & William's royal wedding last year. In my opinion, the best way to appropriately wear those over-the-top hats is to keep the hat's color a pale or neutral color and keep the whole outfit toned down. The risk one runs with these oversized and embellished hats is that it can become overwhelming and downright tacky. Taking the classy approach to this whole affair keeps with the race's tradition and reduces the risk of turning into a fashion nightmare.