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Kentucky Oaks and Derby Fashion: Insider Tips

Updated on March 26, 2013

The Kentucky Derby is not only a major sporting event, it is also a major fashion event. Southerners take their Spring outfits and traditions seriously and that is especially true at Derby time. When it comes to the Kentucky Oaks and Derby, bright and bold is best.

Part of the storied tradition at Churchill Downs is viewing beautiful women in large, oversized hats accompanied by their dates in color-coordinated ties or vests. Crisp, clean suits and flowing dresses are the norm regardless of wind, rain or sleet. However, while dressing up is an important key 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!

Outfit Decisions: This Derby, think big color and strong patterns for both ladies and gentlemen. Gentlemen often wear light fabric suits with a festive, bright tie. Seersucker in grey or navy is a classic look for men, paired with pastel accessories such as a tie, vest or handkerchief. Bowties are also very popular at the track. During Derby, it is not unusual to see men proudly wearing garish checkered or plaid pants or a green blazer with horses on it! Classic, preppy looks with a twist will put you on the right fashion track whether you are in the Infield, Grandstand or the Clubhouse. If a suit is not your style, opt for pressed Khakis with a button down or a polo shirt with a navy blazer to top off the look.

Ladies at the track always wear a hat! Large brimmed and theatrical with flowers or feathers, 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. “Hat hair” is a harsh reality, so loose curls or a ponytail works best to look fresh throughout the day. Typically, a nice sundress with pretty details is most popular, but this year A- line dresses or skirts paired with matching, fitted blazers will be in vogue.

Elegant vs. Funky: 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 at Derby. Some crazy and fun outfits you may see can include feather boas, homemade hats that are replicates of the Twin Spires, disco suits…anything goes!

Shoes: The importance of comfortable shoes cannot be overstated! The walkways and Paddock 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 or muddy yard…be prepared! Seasoned Derby fans attending the race know to make parking plans ahead of time to avoid long treks from parts unknown. The best option is to arrange for private parking, which places you close to track entrances, saving you time and precious effort. In addition, you will be doing some walking even if 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 her expensive heels in hand. For men, a classic comfy loafer worn with socks is best.

Ponchos: No umbrellas are allowed in Churchill Downs but the race goes on rain, shine, hail or snow. There is a saying in Kentucky: “If you don’t like the weather, just wait five minutes.” Be ready for the changing weather by obtaining a clear poncho ahead of time and popping it into a purse or bag…the clear plastic allows for your outfit to shine through while you stay dry and look fabulous.

Lastly, bring essentials like Kleenex, lip balm, sunscreen, a hair elastic and a safety pin for unexpected issues. Pieces of candy, gum or mints will help you out during long drink lines. Also, do not forget to bring a pen to mark up your program with your favorite picks.

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.


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