What to Wear to the Horse Races: Virginia Gold Cup Edition

What to Wear to the Horse Races: The Virginia Gold Cup Edition

I grew up having Thanksgiving dinners on my grandparents’ horse farm in Hume, Virginia. My family and I always attend the Old Dominion Point to Point horse races. I’ve visited the famous horse farms in Kentucky. There’s something about a horse race that feels very comfortable to me. It’s never been about the fashion for me, but about family and a good time. This year, though, the Gold Cup family invited me to capture fashion at the annual spring coming out party for the region’s finest. I told my little brother to put on a suit and away we went.

As we pulled up and oriented ourselves, we were immediately excited to see how many people were there, already tailgating, walking around, smiling, and looking damn good. Everyone was pleased to see the sun after a questionable forecast for this year’s Gold Cup horse races. Right from the beginning of our day, I really enjoyed all of the color, patterns and diverse approaches to outfits at the event. Together with Zack, I captured as many of our favorite outfits at the event as we could while still making time to make friends and enjoy the races. They’re all chronicled below.

The Triple Crown kicked off after the final Gold Cup race ended. We’re all pretty shocked about the Maximum Security upset, but excited to see how Country House does in the remaining Triple Crown races. Preakness Stakes (May 18 in Baltimore) and Belmont Stakes (June 8 in New York) are both close to follow the Gold Cup. There are many other horse races taking shape around the country this spring and summer. Here are a few tips and ideas as you get your tickets, mark your calendar, and plan your outfits:

A few rules about fashion at the horse races:

Have a sense of humor: There’s a way to have a bit of fun with your outfit without mocking the tradition of the event. Take a leap and go with something you wouldn’t wear normally. I love a few of the blazers I saw from Shinesty Threads. The brand also carries women’s dresses and jumpsuits I’m kind of dying over.

Wear the right shoes: You’re going to be walking around a field of grass and dirt all day. If you’re lucky, it’s not going to be wet. Chances are, during the first week of May, you’re going to encounter some mud. I wore my white booties that I literally wear everywhere. They are closed-toe and match with everything. Dirt wipes off of them easily at the end of the day. Another favorite pair I saw are these wedge Hunter boots. They were lady like, but practical.

A hat isn’t just a fashion essential: If you scroll down, you’ll see the winner if the kids hat contest. It took her 3-4 four hours to make that homage to the races! While I photographed and commented on plenty of elaborate hats, I realize after leaving mine in the car that I was in trouble. I am 100% burnt on this fine Monday morning. Take time and invest in a hat. Have fun with it. Embrace it.

Coordinate whenever possible: I’m legitimately mad that my brother and I didn’t plan this well enough. There were so many coordinating outfits among families and friends. I planned my look very little, honestly. It has been such a busy Spring. I snapped up this gingham dress at a thrift store last-minute. It was perfect for the hot temperatures, though. Next year, I will dress bolder, brighter, and definitely coordinate with my crew.

Now, let’s get into the good stuff…

A special thank you all of the people we met and were so incredibly kind to us. We look forward to coming back every year. Another special thank you goes out to the people in the background of these photos. You all are the real MVPs.