With Cinco de Mayo and the Gold Cup occurring on Saturday, DC is buzzing with lots of action this weekend. While various DC venues are hosting Cinco de Mayo parties around the city, the wasps and others are heading to The Plains, VA for Gold Cup. Gold Cup is a local steeplechase race that takes place on the same day as the Kentucky Derby. It’s basically a tailgate party for prepsters so there is always great people watching. My husband affectionately refers to it as “Ascot meets Woodstock.” At the event, you have the premium spots at Member’s Hill, tents full of alumni on University Row, and a bunch of picnickers in between. It takes place rain or shine so there is always a risk of seeing some drunk millennials slipping and sliding in the mud wearing their Sunday best, which also makes for some excellent people watching.
It’s my fourth Gold Cup attendance this year, and learning from my past Gold Cup experiences, I have a lot of practical advice to give regarding what to wear.
Always have a least 3 different outfits in reserve. The weather forecast can change the day before so it’s best to be prepared. Styling different outfits ahead of time will minimize the last minute wardrobe scramble.
Your rain outfit should always include pants and some type of waterproof boot.
Gortex boots and rubber rain boots are perfect. Leave the Louboutins at home since the grounds can get pretty muddy and any sort of delicate shoe can be ruined. If the rain is not too bad, opt for riding boots.
In perfect weather, wear a colorful dress and interesting head piece. The bolder and brighter, the better. If you wear a hat (and you probably should) make sure the hat fits snugly around your head so the wind doesn’t blow it away. Head gear is a key here, but you always want to be comfortable and creative. Not at hat person? Opt for a fascinator instead. Want to want an nontraditional hat this year? Go for it. I’m rocking a Panama hat this year.
Layer up in varying weather. The temperature swings are drastic this time of year so don’t be afraid to layer up. If you’re parking, you may even want to bring a second outfit when it warms up. Gold Cup is an all-day event so it’s not unusual for mornings to start off brisk and afternoons to end up hot and humid. This year, I’m wearing a Paul Stuart wool limestone vest coat in the morning with a reversible equestrian scarf and changing into a floral cotton dress in the afternoon.
Bring a change of shoes. You never know where you might end up after Gold Cup. Various Middleburg residents have house parties afterwards and the Salamander Resort is a lovely place to wait out the traffic going back to DC. Wherever you end up you don’t want to bring your muddy shoes indoors.
Whatever you decide to wear, I do hope you enjoy Gold Cup. It encourages such a boisterous mixing and mingling of well-dressed people outdoors-an unusual sight for this area. And, honestly, the last thing that you’ll be watching is the horse race.
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