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Keeneland’s Fall Meet lasts only 17 days, but there’s certainly a lot of racing fun to be had during those Wednesday-Sunday October stretches. Over the 7 year history of HerKentucky, I find that folks really, really want to know what to wear to the track. In fact, some variant of “What to Wear to Keeneland” is consistently the search that brings the most folks to this site.

When folks ask me in person what they should wear to the track, I tend to ask two questions in response: Where will you be sitting, and what day will you be attending?

At the racetrack, as with most things, location and timing are everything. Wednesdays and Thursdays tend to be a little more casual than weekend race days. The nearer the track you sit, the more casual you should dress.

If you're going to stay near the Paddock --General Admission, Grandstand, or Equestrian Room-- there's no need to dress up very much.  Guys often opt for khakis and polo shirts, and women can wear slacks. You're actually dressing for a horse race in these sections.  These are the areas nearest the track itself, and people are truly there to watch (and bet on) the horses. With that said, don't be surprised to see a lot of dresses and sport coats in the lower-levels. The second floor (General Admission) Sports Bar, for example, often resembles a campus bar or fraternity semi-formal.  While the dress code says "casual", there's plenty of Vineyard Vines ties and Lilly Pulitzer dresses to be seen.

If you'll be dining in the upper-level, enclosed dining rooms-- The Lexington, Kentucky, or Phoenix Rooms-- then expect to dress for a business event.  The Lexington and Kentucky rooms -- dining rooms often reserved for business and social gatherings-- have a "business formal" dress code; these areas require men to don a coat and tie, and skirts/dresses/dressy slacks for ladies.   The Phoenix Room-- another reserved dining room-- is "business casual", requiring collared shirts and slacks for men and dresses/pantsuits for ladies. 

If you find yourself invited to the members-only Clubhouse, you’ll soon find out that it requires coat and tie for men and dressy pants/skirts for ladies.  I find that a skirt suit or a dress paired with a pretty cardigan or wrap is always appropriate for the upper levels.  In general, if you'd wear it to church or a business meeting, you're fine.

This fall, I have two navy dresses on repeat; both are cute Keeneland dresses, depending on your racetrack plans. This navy ponte Draper James dress could work for any section of the track — just dress it up or down with necklaces or scarves, boots or heels — while this Target denim dress is great for a low-key day in the lower levels. (Denim is a huge faux pas for the upper levels, and isn’t allowed in the Clubhouse!)

Of course, it goes without saying that dressing for the elements is just as important as dressing for your seats. Nothing looks more ridiculous than the poor girl who’s freezing in a sundress or melting in wool. You’ll be on the move a lot — sitting and standing, inside and out — so make sure your shoes fit well, your bag isn’t so large that it causes problems, and your outfit matches the temperature and conditions.

Most of all, look good and have fun!!

Shop these great Keeneland styles!