The Sartorial Side of Keeneland

I’ve often thought I’d like to see the cast of Jersey Shore navigate a fish-out-of-water setting. Instead of putting them in their native New Jersey, or flashy Miami, or even Italy (where they’ve done nothing but make all Americans look like tasteless rubes), why not take them out of their natural habitat and send them to the most WASP-ish place on earth, the Keeneland clubhouse? I think America would enjoy seeing the Situation be forced to put on a blue blazer over a velour Ed Hardy track suit. We’d love watching Snooki be escorted out by one of those sweet elderly ushers, mascara streaming down her face, after a day of behaving badly. Actually, let’s face it: she wouldn’t last five minutes.

Keeneland chic is anti-Jerseylicious; it’s low-key, well-bred, and effortless by definition. The perfect outfit for a fall day at Keeneland has been the same since the track opened in 1936: brown leather boots, a tweed dress, a cashmere cardigan, pearls. Too much shine or bling is a fatal mistake. If you look like you’re trying too hard, you’ve missed the whole point.

There’s a difference between dressing for Churchill Downs and Keeneland, and I think that difference can be distilled down to one factor: effort. At Keeneland, everyone does try; the key is to make the right amount of effort: not too little, but definitely not too much.

Churchill Downs, bless its heart, has an anything goes, Bourbon Street quality. Especially at night racing, it’s all gluttony, excess, and pimp hats. If pimp hats seem out of place at Keeneland, it’s because there’s no dance party in the paddock. The paddock there is used for more traditional paddock purposes—horse viewing, people watching, and strutting of one’s stuff. At night racing, the main use of the Churchill Downs paddock is an after-dark dance party with someone called “DJ Squeeze.”

I’m not knocking the dance party. I want Churchill Downs to thrive on days other than Derby Day, and night racing truly brings out people from all walks of life and packs them into the massive new structure that is Churchill Downs. All God’s children go to night racing, and they fill in every section and level of seats according to the pre-appointed social position prescribed by their ticket or, Lord-willing, Turf Club pin. Of course, there are portions of the track that will forever remain pimp hat-free; the best place to watch the paddock carnivale is from a perch high above, where the dress code is more Lilly than Snooki.
What I love about Keeneland, though, is its lack of flash, its quiet dignity. It’s where we Kentuckians go when we want to be on our best behavior, and we know to adhere to its old-school dress codes and decorum. All our statewide vices may be on parade—the bourbon, the tobacco, the gambling—but for the most part we try to bring our best manners with us, too.

We may live in a Jerseyfied world, but as long as there's a Keeneland, there'll be at least one place where a classic strand of pearls trumps rhinestone-encrusted sunglasses, where men are required to wear jackets, and women are strongly encouraged to act like ladies. And we mostly do—even as we carry flasks full of Four Roses in our purses. Snooki could learn a thing or two.