(Reposting this popular post, which was originally written in 2016. This post was brought to you by Shircliff Publishing. For more Kentucky Derby history, download The Kentucky Derby Book by Bill Doolittle for only $9.99; available in Kindle and iBooks editions.)

Here in Kentucky, a lot of us love to wear our Lilly Pulitzer prints to the racetrack. A flattering dress in a bright, preppy print is the perfect outfit for a day at Keeneland or Churchill Downs. Lots of us break out our favorite Lilly dresses for Kentucky Derby week activities. But did you know that Lilly Pulitzer herself had lots of ties to the Derby and thoroughbred horse racing? 

Lilly's stepfather, Ogden Phipps took horses quite seriously. He used Paris, Kentucky's storied Claiborne Farms, for the breeding and training of his horses. He helped found the New York Racing Association and served as Chairman of the Jockey Club for over twenty year, and he lost the famous coin toss that awarded Secretariat to Penny Chenery.  Mr. Phipps owned horses that won the Breeder's Cup and the Belmont, but a Kentucky Derby win eluded him. In fact, in the 2004 book Essentially Lilly, Lilly told her co-author, Jay Mulveny, "I don't race, but everyone in the family has had horses in the Derby. And no one has ever won."

While Lilly never saw a relative win the Kentucky Derby, her half-brother Dinny Phipps did win the Derby with Orb in 2013, only a month after Lilly's passing.

Of course, longtime HerKentucky readers know that Lilly's ties to Kentucky don't stop with her family's racing heritage. Lilly briefly lived in Eastern Kentucky, putting her love of horseback riding to good use as she volunteered as a courier for Mary Breckinridge's Frontier Nursing Service.

And, of course, the Lilly Pulitzer company has put out some lovely Derby- and racing- themed prints over the years; these prints are traditionally cherished by Kentucky Lilly-lovers! 

Shop my favorite Lilly Dresses for Kentucky Derby 145!