As entertaining gurus, Lauren Cermak and I love any excuse to don a fabulous hat and dress and share a cocktail with friends. Thus, the Iroquois Steeplechase is always a highlight for us every spring. For our Derby-inspired table, we drew inspiration from My Fair Lady and focused on black-and-white décor with pops of red. We incorporated traditional elements from the Derby, such as red roses used in the centerpiece and on the cocktail plates, as well as jockey jerseys that are featured in the tablecloth, cocktail napkins and favors for each guest.

Our goal with the table was to keep it feeling fun and well-planned but not too complicated to pull together. It needed to be as portable as possible so that it could be set up in various venues, whether in a private home or in a box in the Steeplechase grandstands. The glassware is acrylic and the flatware is plastic (though they don’t look like it), and all the desserts we included are made as individual servings so they are easy to pick up and eat. We used our mint julep cups as vases on this table, though they can easily double as cocktail glasses if you’re planning to serve the traditional Derby drink.

I always encourage “dressing to the décor,” so when it came time to select our attire for Steeplechase, we worked with Amy Jo Original on custom hats and fascinators. The design process was so much fun, and I like to think that my look turned out to be a modern-day version of what Audrey Hepburn wore in My Fair Lady when she attended the horse races. “Come on, Dover!”

Stylists: Mary Huddleston and Lauren Cermak | Photographer: Lele Fain Photography | Plates and jockey ornaments: For Pete’s Sake Pottery | Cocktail napkins: The Preppy Stitch | Pies: Southern Baked Pie Company | Cake bites: Caroline’s Cakes | Silverware: Sophistiplate | Triple Crown tablecloth: Horse and Hound | Horse silhouette centerpiece: The Virginia Artisans (Etsy) | Award ribbons: Pomp and Pedestal (Etsy) | Table and chairs: Music City Tents & Events | Hat and fascinator: Amy Jo Original Hats | Cocktails: Jackson Morgan Southern Cream | Mary’s dress: Pearl by Lela Rose | Lauren’s dress: Alfred Sung | Shoes: Sarah Flint