What To Wear at the Oaks Anything pink is in style for the Kentucky Oaks. Ties, hats, dresses and even shoes are all pink. The Kentucky Oaks is a little more casual in dress than the Kentucky Derby to dress comfortable and in pink. . What To Expect at the Oaks The Kentucky Oaks once considered “Louisville’s day at the track”, has grown to a 130,000 patron event where most wear pink to celebrate the fillies running for the lillies. A full day of racing, which starts at 10:30AM and the Kentucky Oaks race running around 6:00pm. . What To Do at the Oaks Enjoying the pageantry of the Kentucky Oaks means checking out the horses in the paddock, reading your racing form and making your wagers, drinking a lilly with your friends as you people watch in the stands. .