Derby Experience

Derby Fashion History

Derby Styles Through the Decades

From petticoats and parasols, flappers and fur coats, poodle skirts and miniskirts, pin tucks, polyester and paisley…the Kentucky Derby has seen its share of unforgettable fashions over the years.

The Official Kentucky Derby Photo Archivist, Kinetic Corp., searched its files for some of the quintessential Derby and Oaks looks from decades gone by. Flip through the photos and see if any of these Derby fashions are still hanging in your closet!

Remember, you can purchase historic Derby photos by visiting the Official Kentucky Derby Photo Archives at www.DerbyArchives.com. 

  • Prolific Churchill Downs President Matt Winn shares a laugh with stylish ladies at the 1938 Derby. Photo: Kinetic Corp.

  • The paddock view in 1966. Photo: Kinetic Corp.

  • Fashionable ladies and gents enjoy the clubhouse view of the 1926 Derby at Churchill Downs. Photo: Kinetic Corp.

  • Flappers study the racing program in the Churchill Downs paddock circa 1926. Photo: Kinetic Corp.

  • Not much has changed in the Churchill Downs Jockey Club -- except the fashions -- since the mid 1920s. Photo: Kinetic Corp.

  • People watching in the third-floor box seats on Derby Day in 1938. Photo: Kinetic Corp.

  • Pre-World War II Derby fans are pressed against the fence, hoping to see a winner. Photo: Kinetic Corp.

  • Seeing double at the 1940 "Run for the Roses." Photo: Kinetic Corp.

  • Fans watch the action from the bleacher seats at the 1950 'Run for the Roses.' Photo Kinetic Corp.

  • Smiles and styles from the Winner's Circle in 1966. Photo: Kinetic Corp.

  • Mini-dresses and striped pants are all the rage in 1970. Photo: Kinetic Corp.

  • Love that plaid jacket! The view from the Skye Terrace is very coloful in 1976. Photo: Kinetic Corp.

  • The Winner's Circle after Spend a Buck's victory in 1985. Photo: Kinetic Corp.

  • Grandstand fashions from 1988. Photo: Kinetic Corp.