The first weekend in May lends itself to the most stylish two and half minutes in sports. The Kentucky Derby is steeped in tradition both on and off the track. The pageantry of the horses is just as spectacular as the fashionable patrons that cheer them on.

Derby is the best place to go all-in with fashion. A great headpiece will command attention better than any other accessory. Be bold; everyone is on display at Churchill Downs!

Which comes first: the dress or the hat?

Some will tell you to begin curating your look around your hat, while other seasoned vets will say staring with your dress makes the most sense. Who is right? They both are.

Derby prep can begin as soon as you’re ready. Selecting a color theme creates a great starting point for the rest of your look.

Consider your clothing, shoes and jewelry when selecting your headpiece. Materials, embellishments, colors, patterns and textures should be taken into consideration when choosing your hat or fascinator. Styling your Derby look takes a careful eye. Your outfit should reflect your personality as well as where you will be watching the race; an infield experience will require something entirely different than enjoying a day in the Turf Club.

Take into account where you are sitting. If you will be outside and uncovered, you will need to pick a fabric that allows you to move freely and can take some weather-induced situations. For example, wearing all satin in the heat of the day will show everyone where you are sweating. But if you are in a climate-controlled environment, a more delicate fabric would be acceptable.

Once you have your color and outfit selected, you can begin your quest for the perfect headpiece. If you have the time and resources to customize your headpiece, working with a hat designer of your choice is the perfect way to create a unique one-of-a-kind look that will enhance your Derby Day experience. A few things to keep in mind when selecting your hat:

If you are outside and uncovered, a hat with a brim is a great option. You can make a statement while keeping the sun at bay. If you choose a full-fledged hat, take into consideration your height-to-hat-brim ratio; if you are 5’8 or taller, you can opt for a wider brim and still maintain structural balance. If you are shorter, keep your brim on the smaller side to keep the look proportionate. To keep your look elevated and attention drawn upwards, avoid hats that droop on both sides.

Hats can be heavy when you wear them all day. A lighter, more whimsical option is the beloved fascinator. Fascinators can create a bold statement or balance a look in perfect harmony. Since they are typically attached to a headband, fascinators can be a great option for an easy, effortless statement.

Get in Shape

Whether you choose feathers or flowers, knowing what suits your face shape enhances the power of a fascinator.

  • For oval-shaped faces, choose a saucer fascinator or hat worn slightly to the side.
  • For square-shaped faces, opt for a larger-brimmed hat or large-scale fascinator. Asymmetrical styles are also complementary.
  • For round faces, a pillbox-style fascinator or hat is a great choice, as well as brims that slope away from the face with netting.
  • Heart-shaped faces look great in almost everything!

How about Hair?

How to style your hair with your headpiece:

  • If you’re wearing a hat, a low-wrapped ponytail or side chignon is timeless. You can opt to style your hair down with curls; however, the hat is the star of the show and should be given every opportunity to shine.
  • If you are wearing a fascinator, wearing your hair down with curls or waves is an excellent way to highlight your hair and your headpiece.
  • You can wear your hair in a low bun with a fascinator; this look is best with statement earrings that coordinate with your headpiece.

No matter how you choose to top off your Derby look, be sure to wear it with confidence; that’s the key to looking your best in any situation! •

Shannon Kessler is the Founder and Owner of Primp Style Lounge in Chenoweth Square. As a personal wardrobe consultant to men and women around Louisville, she knows the importance of helping people identify their look and embrace their style.

Find Her On Instagram: @shannonwkessler

Learn More About Primp: primpstylelounge.com

Posted on 2023-04-01 by Shannon Kessler