The Kentucky Derby is legendary. But it’s not only about the horses— it is also about endless people watching, unique fashion and great memories. Historically, racing enthusiasts of days past would dress in their finest outfits to “see and be seen” and horse racing was a huge social event. That tradition is still true today for the highly anticipated annual Run for the Roses. When it comes to dressing the part in the modern era, bright pastels, bold patterns and equine-inspired items are always chic and in style for the Kentucky Oaks and Kentucky Derby.
Part of the storied tradition at Churchill Downs is viewing beautiful women in large, oversized hats accompanied by their dapper dates in color-coordinated ties. Crisp, clean suits and pretty, structured dresses are the norm regardless of wind, rain or sleet. However, while dressing up is an important element of the Kentucky Derby experience, it is also crucial to be comfortable and mix fashion with function. The following tips can help you make the most of your days at the track while looking your best for the Kentucky Oaks and Derby!
The Kentucky Oaks is considered the sister race to the Kentucky Derby and is always held the day before the Derby, the first Friday of May. The races of the day feature “fillies” only, earning the nickname “Ladies Day” at the races. A local favorite for decades, it’s popularity has grown since partnering with the American Cancer Society. Cancer survivors are acknowledged in a special tribute parade on the track. Pink is the color theme for men and women alike, so be sure to pick out an outfit with this springtime color to show your support. Kentucky Oaks Day is considered by some to be more “refined” than the Derby and is reminiscent of an older time of elegance and charm.
For the Kentucky Derby, outfits boast big color and busy patterns or stripes for a traditional, festive look that makes a statement. Gentlemen often wear light fabric suits with a printed or pastel tie. Seersucker suits in gray, yellow or navy are a popular look for men on Derby, paired with accessories such as a vest, handkerchief or colorful socks. Bow ties are also very, very popular. During Derby, it is not unusual to see men wearing outrageous checkered pants or a bright green blazer with horses on it! Preppy looks with a twist will put you on the right fashion track whether you are in the Infield, Grandstands or the Clubhouse. If a suit is not your style, opt for pressed Khaki pants with a striped button down or polo shirt paired with a sport coat to top off the look. You will never be accused of being overdressed for a day at the races, especially the Kentucky Derby! Many women prefer to wear a sundress or a well-fitted shift but a well-tailored suit is not uncommon. Purses are simple and petite with enough room to throw in a pen for the program and keep your cash handy for the betting windows.
Hats, Hats, Hats! Ladies prefer large brims and theatrical flowers or feathers– and bigger is always better when it comes to making a fashion statement on Kentucky Oaks and Derby Day. If a huge hat is too much for you, then a delicate Fascinator is a beautiful alternative. These beautiful headpieces are smaller and more delicate than a full sized hat and often clip to the hair or are attached to an easy to wear headband. To avoid the dreaded “hat hair”, loose curls or a ponytail works best to look fresh throughout the day. Men wear hats too, gentlemen tend to don a Fedora or Bowler hat to top off their look. Sunglasses are also a part of the complete ensemble. If rain is in the forecast, a clear poncho will keep you dry and looking fabulous. Be sure to pop a few in your bag.
While for most, the Kentucky Derby is an elegant affair, some choose to express themselves in a whimsical way and nothing is out of the ordinary on Derby day. Outlandish outfits seen that day can include gigantic theme hats that are an ode to the majestic Twin Spires or a favorite horse. Fans drape themselves in feather boas or wear matching gold disco suits…anything goes! Creativity abounds as people work year ‘round creating a one of a kind, fun statement in fashion to celebrate this special race.
Looking good is key but feeling good all day is imperative. For a full day of horse racing, the importance of comfortable shoes cannot be overstated! The paddock and many other areas at Churchill Downs are partially old brick and cobblestone, not best suited for stilettos or new loafers. Parking is sometimes in a neighbor’s uneven grassy yard so be prepared. In addition, you will be doing some walking even if you are seated in the best areas. The key is to wear something that has proven to be comfortable in the past without sacrificing too much style. For women, a wedge is a great option as well as a chunky heel. Some veteran Derby-goers will bring flip flops or flats in their purse for later in the day. Pity the poor girl going barefoot with expensive heels in hand. For men, a classic loafer that has been broken in previously is best and be sure to wear those colorful socks!
The Kentucky Derby is a magical event like no other, full of tradition and pageantry. With the right preparation and a bit of personal style, you will have one of the best experiences of your life to remember and share for years to come.