Derby Dressing

It’s Derby Day!  The Kentucky Derby is one of my favorite American cultural institutions. Although I’ve never been to the Derby, it remains high on my Must Do list.  I love the fanfare of the event and the old-fashioned allure.  I adore both the Derby fashions and the thrill of the most exciting two minutes in sports. And I just love equestrian culture and design.

In honor of today’s Kentucky Derby, below are a few of my favorite images via Harper’s Bazaar collection of celebrities attending horse racing events, as well as my own selection of pieces that would work brilliantly for those attending the Derby or a Derby party:

Liz DerbyElizabeth Taylor

Di DerbyPrincess Diana

Nicole Kidman DerbyNicole Kidman

In choosing a Derby dress, I prefer a sleeveless dress with a shorter, above the knee, daytime hemline.  Since the Derby is a Southern, old-fashioned affair, I would err on the side of looking like a Southern Belle. Here are my picks for an afternoon at Churchill Downs.

Derby Dress 1

I would wear this Lilly Pulitzer dress with some wedges and either a white hat or a pink hat to create the ultimate preppy color combo:  pink and green.


Derby Dress 11I find this Giambattista Valli dress to be the most sophisticated of the bunch.  For that reason, I would throw on an outrageous hat and high heels.

Derby Dress 5This Kate Spade dress has such a classic silhouette and the orange and white stripes make it more festive.  I like how the dress is shown with orange pumps.  A matching orange hat would be the perfect way to top it off!


Derby Dress 8This black and white ruffled Halston Heritage dress is more fashion forward than most Derby dresses and it mimics the particular flounced flair that many Derby hats display.  I like it with sandals and an all black hat.


Derby Dress 7I always love a pink Derby dress, and this Cynthia Steffe peplum dress is no exception.  I would add some bow bedecked heels and a pink and white hat.


Derby Dress 3 Oscar de la Renta is the master of ladylike elegance.  The trimming on this dress is lovely.  I would pair the dress with a white hat and simple pumps, perhaps a white pair in the pointy toe style pictured above.


Derby Dress 6This Halston Heritage dress has a throwback silhouette but the cutouts make it more modern.  I could see this dress with a black and white hat and some heeled sandals.


Derby Dress 10Landscape prints, particularly those featuring flowers, seem appropriate for the Kentucky Derby.  This Erdem dress showcases flowers that are more sophisticated than sweet.


Derby Dress 4

A mint green dress pairs well with a mint julep in hand.  I would wear this Alice & Olivia dress with a white hat and white heeled sandals.


Derby Dress 2Or, why not wear mint juleps on your dress?  This dress by Lilly Pulitzer is cheeky and fun.


Derby Dress 9This Collette Dinnigan dress is one of my favorite picks for its Derby appropriate farm scenes, which I like to imagine are horse farms.  I just keep finding more toile pieces!  I would add a pair of blue pumps and a green hat.


A fanciful hat is a must at The Kentucky Derby:  Any of these would be certain to turn heads:

Hat 1The Hat Shop

Hat 8The Kentucky Derby Official Store

Hat 13Barbara Feinman Millinery


Hat 5Kentucky Derby Official Store

Hat 2The Hat Shop



Hat 14Barbara Feinman Millinery

Hat 9Kentucky Derby Official Store

Hat 12Kentucky Derby Official Store


Hat 7

Kentucky Derby Official Store.   

For more Derby fashion inspiration, visit The Kentucky Derby website.

I just love events with pomp and circumstance.  Do you?

Have you ever attended The Derby or a Derby party?  What did you/would you wear?

2 thoughts on “Derby Dressing

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