Tomorrow is the first day of Keeneland's Fall Meet, y'all! Now, Lexington in October is the absolute prettiest scenery you can hope for, and the Fall Meet is my absolute favorite. And, in all the years I've been writing about Kentucky, the question I get asked most often is "What should I wear to Keeneland." Here's a handy guide to help you crack the Keeneland Dress Code.

When someone plans to attend their first race at Lexington's storied Keeneland Race Course, I ask three questions to help them plan their wardrobe and Itinerary: "Where are you sitting?"; "What are you doing?"; and "Will the weather cooperate?" As you'll see, those three questions factor into every piece of your Keeneland experience.

1. Where are you sitting?

This is the most important question to help you gauge your Keeneland wardrobe and experience is where you'll be sitting.

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 or skirts. 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. In recent years, a culture of dressy tailgating (think Steeplechase) has popped up among college students and twenty-somethings, and the second floor (General Admission) Sports Bar 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 sundresses 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 or pantsuits for ladies.

Wear to the Dining Rooms

The track's members-only turf club, the Keeneland Clubhouse, similarly 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 golden.

Wear to the Clubhouse

2. What are you doing?

That seems an odd question; you'll be watching the horse races, right? Well, there's a little more to it. Are you going to walk frequently from the paddock to your seating area? Then you don't want to wear high heels. Will you be tailgating? Then you might want to wear wedges or wellies. The same applies to your parking space! I like to suggest a small handbag or clutch; you don't want to have your hands full with an oversized bag!

3. Will the weather cooperate?

Pretty often, Keeneland attire is a day-of decision. October in Kentucky is a pretty tricky weather situation. It could easily be 80 degrees one day, and 50 degrees the next. You’ll need sunglasses, of course, but also potentially a sweater or wrap or a sundress, depending on the day you visit. It’s really easy to get dehydrated on a sunny autumn day at Keeneland. Remember to drink plenty of water, especially if you’re imbibing, and don’t forget the sunscreen!

Most of all, remember to enjoy what I’m sure will be a pretty wonderful day at the track!