What to Wear at the Virginia Gold Cup

So What Should You Wear to University Row at the Virginia Gold Cup?

Looking good is a huge part of University Row and with so much emphasis put on attire, we want to break it down for you and describe what you should and should not wear on Race Day. University Row is the place to be at the Virginia Gold Cup so you’ll really want to dress your best!

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As previous attendees will note, wearing frayed shorts and a worn out T-shirt will not get you far at the Virginia Gold Cup. Instead, true Gold Cup connoisseurs take this as an opportunity to “Dress to the Nines.” Women are encouraged to bring out their finest linen dresses, charming hats and accessories, and men should see this as an opportunity to show off their seersucker suits, madras sportcoats, and spring shirts.

Gold Cup is an annual inauguration of the outdoor social season for DC Urbanites, bringing together horse racing, fine southern beverages, and socializing so it’s important that you make a good impression! How better to catch the eye of a woman than with your sporty Nantucket red trousers? What better way to bring in the beaux than with a sweet sundress or sassy wide brim hat? You’ll want all eyes to be on you and your attire will help you achieve that!


Light summer sundresses in crisp cotton or floaty chiffon are perfect for University Row, and this year, pleats, ruffles, and flower patterns are the “in-styles.” You can find spring sun dresses all over DC, but some standout shops include Lilly Pulitzer and Eloquii. Many of our guests also shop for dresses at Tuckernuck, Vineyard Vines, or JCrew.

The Virginia Gold Cup is run on grass, and all of the tents are on grass also so leave the stilettos and kitten heels at home, and opt instead for colorful ballet flats, metallic sandals, wedges or even fancy mules, which are “all the talk” this season. If there is concern of mud due to weather conditions, stores like Target usually have rain boots in bright colors and patterns that should coordinate with any ensemble. Town and Country Magazine and Carrie Colbert also give give some good pointers on what to wear at the Virginia Gold Cup!

Brightly colored clutches are cute, but are likely to be left on a table or lost on race-day. Crossbody handbags and half-moon bags with a strap allow hands-free storage so you can do better things with your hands, like enjoy food/drink and blow that cute jockey a kiss! Check out Kate Spade, Georgetown for brightly colored bags and accessories!

And for additional accents, Kendra Scott , has a variety of lines to assist you! Accessorize with some of our favorites — the “Elton Bracelet” and “Payne Necklace” (Kendra Scott) — to finish out your look.


Gold Cup is not the place for jeans and polo shirts, but it is the place to break out your loudest pants (seersucker, madras, critters and bold colors highly encouraged) and crisp button down shirts. If you aren’t the fancy-pants kind of guy, khakis and a pastel-colored button down shirt accessorized with a bow tie, ascot, needlepoint or colorful woven belt will do just the trick!

Leather shoes are de rigueur but may come in several interpretations – boat, bucks, spectators, or cap toes. If you plan on visiting Member’s Hill while at the Virginia Gold Cup, a sportcoat is highly suggested and while a blue blazer is always in style, a seersucker or madras patchwork will help you really stand out! Don’t forget to tuck a matching pocket square into the breast pocket, and to wear a hat! Oh, and of course, remember gentleman, if a young lady is cold, make sure to give her your coat!

Check out this link from the Art of Manliness on some horse race attire for gents, or take a look at what Esquire has to say for what to wear at Gold Cup…


Here are a couple of other stores with attire for both men and women.

Brooks Brothers, Old Navy, and Vineyard Vines.

University Row’s large space gives us all air to breathe, but that isn’t an excuse to forget sunscreen. We want you to feel refreshed from a fun day at the Races, and not cooped up on Sunday achy from a sunburn!

For some extra thoughts on what to wear at the Virginia Gold Cup, the Middleburg Eccentric community newspaper has some interesting ideas for you. Or, you can always look at what the folks over Southern Living, or at Kentucky Derby themselves, have to say on what to wear on Race Day!

If the weather is damp – you can plan to incorporate a cute pair of wellies or boots into your ensemble.


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