Top Fashion Moments of Oaks & Derby 144

Eden, Justin, and Ryan Bridgeman “The Trifecta.”

Photos by Tony Bennett, Kathryn Harrington, Scott Henson, Louis Tinsley, Christian Watson and Hunter Zieske

On both Oaks and Derby 144, our photographers captured thousands of swoon-worthy and sophisticated ensembles. Some race-goers become so enraptured by the looks of their fellow spectators that they nearly forget to pay attention to the Thoroughbreds. While the Great Derby Downpour dampened the big day, it didn’t stop fans from bringing out their most festive, fashionable and over-the-top outfits.

Stephen and Cassandra Amell

Eleanor Wells.

Sammi Barber.

Victoria Justice.

Bart Burton with Shannon Burton in Rose Dress. Dress sponsored by the Churchill Downs Foundation made by Amy Streeter.

Bonnie Jill Laflin.

Christina Wilson.

Nikki and Joey Wagner.

John and Nick Hansen.

Brandon Hershman, Hillary Mullins

Johnny Weir with his likeness on fashion.

Carson Grisham.

Morgan Grillet, Cara Wilson, Elizabeth Cruse

Tara Lipinski and Johnny Weir

Amanda Cerny

Aisha Tyler

Shelby McGuire