Middleburg Spring Race Attire

2015 Middleburg Spring Races- Anne Sittman, Nick Greenwell, Brandy Greenwell in the Old Town Crier

Riders up!! Spring in Virginia’s horse country is full of many equestrian events including the Virginia steeplechase circuit. Starting in March and going into May, there is a meet every weekend full of riders, spectators, tailgaters and most of them are dressed to be seen. As someone who has dressed many ladies for the occasion and has been to plenty herself, it can be challenging to find the perfect outfit for the terrain, weather and occasion. So here are some helpful tips on how to dress for the races.

First, I know this has been said before, but PLEASE, ladies, do not wear heels that can sink into the ground. This causes pulled calf muscles and that mobile hiccup effect where every other step creates a jerking motion to release your heels from the clutches of the soft, spring earth. Even if it is a wedge, ones that are too high to walk in over rough ground are reserved for professionals to accomplish with grace. And perhaps most importantly, your shoes must be comfortable enough for all day on your feet. No one, I repeat, no one likes to see the drunk girl, sling back in hand, stumbling toward the porta- john where she generally enters barefoot. It’s just gross. Your foot fashion can make or break the day. Trust me.

Next, hats are often a staple at the races. If you are not confident enough to rock out a hat with pride, leave it at home as you will look like a little girl playing dress up instead of a Kentucky Derby diva. They are meant to accent your eyes and are NOT to be worn on the back of your head like Madonna or Boy George in the 80’s. And along the same lines, just to be proper, I should mention that a ladies brim should never be wider than her shoulders. That is an old rule, but still one to remember in order to get the most flattering style for you. Now, day of: I sincerely advise you to make sure they are secure somehow either by hat-pin or proper fit. And no, elastic bands under your chins do not count and one should be publically flogged for even thinking of it. It is never flattering to see a lovely headpiece blow like tumbleweed from tailgate to tailgate or decorative feathers take flight without their avian owners.

Anyone that has been to Glenwood Park, Woodley or Member’s Hill at Great Meadow knows there can certainly be a breeze pass through the day, no matter what the temperature. I spoke of loose hats, but what about loose skirts? Mother Nature can be a prankster in the spring and you will get Punk'd if you don’t dress accordingly. Skirts that are too short and flowy nearly always lead to an obscene moment revealing which style Hanky Panky, or in some cases, Spanx you prefer. And perhaps a finishing school lesson needs to be resurrected, please bend at the knees when picking things up. Full moons should be reserved for werewolves and downward facing dog. I guarantee, even if you think no one sees your blunders, one of the hundreds of guests did and have already put your wardrobe malfunction on YouTube.

So have fun, be safe and dress appropriately this month wherever you are racing.