Finding the Right Shoes for Derby Day

Wearing comfortable, stylish shoes is a requirement for a positive Derby experience.

The cobblestone pathways of Churchill Downs can make finding the right shoes for Derby a little bit harder than you would think. And if you’re planning on joining the large crowd in the infield, go ahead and pack your rain boots for good measure.

Comfort is going to absolutely be the key to successful Derby day in your shoes. I 100 percent recommend packing a pair of comfortable flats in a small bag to throw on after the races conclude. Unless you’re arriving in extreme style, the chances of you having to walk from your car and to your car from the track, are highly likely. The worst thing I can imagine is sore feet and a long walk after a day full of mint juleps and exciting races.

So when you want to look your best self, but can’t imagine standing in heels all day, what do you do? You either rely on your trusty pair of kitten heels or wedges, or find a new pair that won’t destroy your feet. Finding a new pair means trying on, considering several options at once, and possibly a hefty price tag. My tip is to plan ahead, and here’s how you do it.


You have the dress, you have your hat, and now you’re stuck with what shoes to wear. You can’t imagine wearing a 5 -inch heel all day, and you absolutely can’t envision yourself in a pair of flats all day. What to wear can easily be overwhelming. So you start with the basics first, and plan accordingly.

First, find a few options that go well with your dress. What color, shape and design are you looking for? Pin a few ideas online and photograph your dress with your at home options too. You can best visualize a look when you see it in a picture. From there, try on your options.


Whether in a department store or in your own closet, look for a pair of heels that have good support first and foremost. If there’s some substance and width to the actual heel, you are better off. Block heels are really in right now, and they always provide more support. Try a wedge sandal, but make sure the wedge isn’t too high. Turning an ankle in front of lots of dressed up folks isn’t fun either.

If you’re nervous to even try a heel, go for something short, and strappy. The straps make the shoe and your legs appear a bit longer. You can also look for something with a little color or a print. Depending on your dress style and your hat, your shoes can be just as fun. Remember, I said originally that your Derby day outfit is a head-to-toe representation of your style. Shoes count too!

Below I’m sharing my current favorites online for Derby day. All of these options offer good support, great quality, and will last you a few hours of wear.

Finding the perfect Derby shoes is very important.

The horse broke well today,” Gaffalione said. “I had the horse inside, Dunph, going to the lead and then (Gun It) showed a little bit of speed. When I saw they were intent on going I just tried to get him back and got him to relax. He came back to me nicely and settled well down the backside. Got a little keen going into the far turn and wanted to move a little early. But I didn’t want to take too much away from him so I tried to sit as long as I could. He was waiting on horses down the lane but I kept him at task and there was plenty of horse there.”

“Mark (Casse, the trainer) and his team have done a great job,” Gaffalione said. “They’ve had a ton of confidence in this horse the whole way. It’s just an honor to be able to ride the horse. He’s just so professional, trains great and he’s a pleasure to be around.”

Tyler Gaffalione, Rode of War of Will to victory in the G2 Risen Star Stakes at the Fair Grounds

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