6. What should I wear to the Kentucky Derby?
The Kentucky Derby is a wonderful opportunity for a woman to express her own take on a genteel Southern belle. There are no set-in-stone, hard and fast rules. These days, Kentucky Derby outfits run the gambit from casual sundresses to cocktail dresses and even more formal. Your outfit choice is somewhat dictated by where you plan to spend the day. In the reserved seating areas (particularly the suites), dressing will be a little more upscale than it is in general admission or infield area. .
What you might not have realized about the Derby is that it is actually a two-day event, meaning you’ll need not one, but two outfits! That’s right: two hats and two dresses.
As alluded to above, Friday is Kentucky Oaks day. This is a full day of the fillies (female horses) racing. In the spirit of it being ladies day at Churchill Downs, the track partners with a charity to raise money for the education, support, and empowerment of young women nationwide in prevention of breast and ovarian cancer. The race track itself and all the attendees tend to deck themselves out in pink on Friday, creating a beautiful sea of pink everywhere you look!
Then, of course, Saturday is Derby day. Attendees often gravitate towards looks with floral prints or the color red to tie into the red roses theme of the day.
You might ask: which comes first? The dress or the hat? That’s a great question… I go both ways on this.
For instance, for Kentucky Oaks day this year, I knew I wanted to wear this stunning Philip Treacy hat in the requisite color of the day, pink. When I spotted this gorgeous pink and navy Sachin & Babi dress, I knew I had nailed down the essentials of my outfit.
However, for Derby day, I took a different approach. As part of Donegal Racing, our team colors are yellow and green. Furthermore, my dear friend Donae from The Vintage Contessa who attended the Derby with me this year offered to let me borrow this fabulous Hermes 35 cm Birkin bag in yellow and green — perfect for Donegal Racing! So, with the color palette and bag chosen, I selected this elegant Tibi open-back floral dress. And then finally, milliner Eugenia Kim custom designed this hat to go with my look for the day. I loved seeing the talented Eugenia Kim’s modern, minimal, chic take on a Derby hat!