Visiting in Horse Country

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My wife and I recently took a little vacation to the heart of Virginia horse country. Middleburg, ground zero for the moneyed portion of Virginia’s horsey set, is exactly what you expect an exclusive equestrian hamlet to be. With beautiful rolling green hills, dotted with heart-stopping estates and crisscrossed with white fencing, it easily evokes visions of Ralph Lauren ads.

We stayed at a wonderful country estate named the Goodstone Inn. I say estate because that’s really what it is. Set on 265 acres, the Inn is an award winning collection of residences, barns and stables spread across the property. There are actually five buildings in which to stay, each with its own distinct theme. The original carriage house serves as the Inn’s living room and also houses their exceptional restaurant.

If you happen to be in the DC area, make sure to stop by for a few days; it is a different, more genteel and refreshing world. A warning though; you’ll quickly want to become the landed gentry.

In fact, visiting horse country often inspires one to dream of misty morning walks to the stable and a rambling family house stocked with giant oil paintings, antiques and sterling silver knick knacks. You might also feel a strong desire to ditch your current wardrobe for something more earthy – heavy on the leather and waxed cotton.

The storied anglophiliac horse culture of Maryland and Virginia can easily bring these feelings to the surface in almost anyone. But before you go galloping off after crafty foxes (or, nowadays, pre laid artificial fox scent trails), you’ll need to look the part.

Dressing for this kind of an environment is a balancing act because good horse country style is really a blend of bespoke and stable boy. One of the best suggestions I heard for getting the right mix came from a local: think of Prince Charles, then put him in a pair of jeans. Not 7 For All Mankind or anything like that, just plain old jeans.

And that really is the style guide I would suggest. Most of the Middleburg horsey set is very well off – horses are not really a poor man’s accessory – and they revel in their earthy, down home English/American lifestyle.

When we visited, it was transition weather; warming days and cool evenings. Barbour jackets, sans liners, and leather paddock boots tended to form the core of many folk’s ensembles. Jeans or trim khakis, paired with simple merino or cotton sweaters or well tailored shirts, added to the dressy casual vibe.

Most of the people I saw had on clothing that looked nice but not necessarily new. To me this was very refreshing and appeased my New England aesthetic for worn-in classics over of-the-moment flash. Several of the women I saw around town were wearing jodhpurs and lovely riding boots; just back from an afternoon cantor I guess. The men were more Ralph Lauren-ish, but in a practical way. They often looked as though their clothing was tossed on without thinking, but from a wardrobe that had only great clothes in it. I think we all need a good hacking jacket in the closet.

That’s a good lesson for all of us; if you only choose things that are of high quality, great style and good material, your wardrobe should always yield a great outfit for any occasion. I recall one gentleman who had on a slightly muddy pink hacking jacket, white cotton oxford, old jeans and barn boots.

Stepping out of a dark green Range Rover he looked elegant and natural, not at all contrived. I think that’s a personal goal most of us aspire to.


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Chris Hogan, an association executive based in Washington, D.C., blogs at OffTheCuffDC.com. A lifelong interest in style and clothing led to sales and management positions at several Ralph Lauren stores and an active wardrobe consulting practice