Figuring out what to wear to Keeneland can be very tricky. Either you’ve never been before, or you don’t know what to expect as far as the weather goes. I’m here to tell you the weather will always be unpredictable for Keeneland. It’s smart to pack two (or three) outfits, with layers. You can never be too prepared.

I grew up at the track, spending long days there with my Dad. I even worked at Keeneland in my early 20’s. I spent most of my time behind the scenes in their retail operation during the offseason, and then I coordinated their trunk shows during the race meet. I know firsthand how hard it can be to dress for Keeneland, but how fun it is to dress up for a day at the races. I personally tend to steer away from the norm and the more preppy styles, but do not worry. If you’re reading this, I’ve collected a number of dresses, skirts, coats, accessories and shoes for any budget or style.

You should also note that what you plan to wear to Keeneland should also be based on where you plan to sit, stand or hang out. The clubhouse for instance is dressier. No jeans allowed, and I recommend a dress for the ladies. If you plan to hang out in the grand stand, you can definitely be more casual. I also should say that if you plan to tailgate, do not wear a skinny heel. You will in fact, SINK into the grass. You will be on your feet A LOT, so plan to wear a comfortable shoe or a block heel at least.

That being said, below is a boutique of pieces I put together that I would wear any day to Keeneland. Simply click the image to shop the style. Feel free to reach out to me (alex@lexwhatwear.com) if you have a question about styling or preparing your wardrobe for the upcoming Keeneland race meet.

Hope to see y’all at the track!

XO, ALEX