Be A Stylish Spectator

In less than two weeks, Churchill Downs will host the Kentucky Derby, and in addition to the highly anticipated race, the attire is sure to be absolutely riveting. To help us plan our Derby ensembles, we asked TSG Equestrian editor Molly Knott for advice on how to look fashionable while attending the races; here are her recommendations:

  • It might go without saying, but a hat is absolutely essential. Wearing a hat to the Kentucky Derby is not only tradition, but also considered to be good luck! Wide-brim styles are most commonly associated with race day style; however, smaller “fascinator”-style headpieces, popularized by the always-stylish Kate Middleton, are another very fashionable option.
  • Let your hat be the scene-stealer. To balance it out, keep dresses to a slim silhouette—a fit and flare style is a modern and feminine choice. Most derby-goers opt for above-the-knee length, but if you like to stand out, pairing a midi with peep toes and a fascinator strikes a charming and vintage note.
  • Keep jewelry simple. Derby style can veer into dangerous territory when the look has too much going on. Skip the statement necklace and focus on studs and a clean necklace or bracelet.
  • Pack a pair of flats. While the race itself only lasts about two minutes, the festivities go on all day and heels can be murder on Churchill Downs’s cobbled paths. Veteran Derby goers pack a tote in addition to their clutch to stash flats and a light layer if the weather looks iffy.
  • Dress your gentleman. Derby day is an opportunity for men to have a little fun with their style too, but if you have a date, don’t be afraid to help them keep it classic. Pastels and cheeky patterns on bow ties and belts are signature looks for the derby gent. A light linen suit can be an elegant counterpart to your own carefully constructed look. Seersucker can be pulled off, but only if expertly tailored.

Expert tip from TSG EQUESTRIAN editor Molly Knott photo by BRENDA CARPENTER PHOTOGRAPHY.