Each spring and fall, Virginians don their “afternoon dress” or “Sunday best” to celebrate the state’s steeplechase tradition with posh horse races. Social affairs, these events are filled with fashion and tremendous tailgate spreads, complete with lawn games and farm-to-table food and drinks. The sport is one of elegance and beauty as equestrians race over lush fields and hills. This season, the custom continues with the Foxfield Spring Races on Saturday, April 28, and the Virginia Gold Cup on Saturday, May 5.

(Above, bottom photo by Richard Clay, courtesy of VA Gold Cup)

The proximity to the horses on race days make for an exhilarating experience. Reaching speeds around 45 miles per hour, the horses test the limits of speed and agility and tradition includes spectators placing friendly wagers on their favorites and then raising their glasses to the fastest. In addition to the competition on the field, hat and tailgating contests are added entertainment.

No matter the season, this 250-year-old tradition continues to excite and entertain equestrian lovers. Be sure to check our Facebook and Instagram for special ticket giveaways for upcoming races.

To learn more about Steeplechase, get Book 4 of Wine & Country Life. Scroll on to see our horse race fashion guide!

(Above, bottom photo by Chris Weber, courtesy of VA Gold Cup)

From broad-rimmed hats embellished with lively accessories to bright seersucker suits, the preppy fashion showcased at Virginia horse races is always a staple of the events. We put together some of our must-have pieces to help you plan the perfect look.

For Her (1–3) & For Him (4–6):

  1. Spring/summer dress: Forever Holiday Dress from Verdigris
  2. Broad-brimmed hat: “The Vineyard” hat with “The Traveler” scarf from Wine & Country Collections
  3. Pearls: Morganite & Akoya Pearl Stud Earrings in Gold from Ana Cavalheiro Fine Jewelry
  4. Watch: Tissot Quickster Chronograph Quartz Watch from Schwarzschild Keller & George
  5. Bow Tie: Lewis Bow Tie by Collard Greens from Natty Beau
  6. Button-up shirt: Mint Crinkle Plaid Print Long Sleeve Shirt by Stone Rose from Verdigris. ~




Wine & Country celebrates elevated living in Virginia Wine Country. Wine & Country Life, a semi-annual life & style magazine, and Wine & Country Weddings, an annual art book celebrating elegant Virginia weddings, are complemented by the Wine & Country Shop in Ivy, VA—a beautiful lifestyle boutique that brings the pages of the magazines to life. The Shop features over 40 Virginia artisans with everything from tailgating essentials and Dubarry attire to locally made foods and award-winning Virginia wines and craft beverages for your next event. Wine & Country covers the grape-growing foothills of the Blue Ridge Mountains from Lynchburg to Leesburg, including points in between like Charlottesville and Middleburg. Ivy Life & Style Media also creates other projects, including CharlottesvilleFamily.com, a collection of local resources including a popular calendar of events, family services guides and features on education, health and family day trips for parents and teachers in Charlottesville, as well as the CharlottesvilleWelcomeBook.com a guide to resources for Charlottesville tourists and newcomers.