Not to put any extra pressure on you, but the nation is pretty much watching on Derby day. It’s pretty much the last moment you’d want to make a major social faux pas. (Again, no pressure.)

Fortunately, we’ve been there. We can help you naviage it all, from the infield to Millionaire’s Row.


We’re assuming you’re going to be wearing a giant hat or fascinator. (If not, that’s your first mistake.) We’re also going to go ahead and assume you don’t wear big ol’ hats on a day-to-day basis.

Your hat increases your square footage. Be aware of your immediate blast radius when moving about Churchill – you don’t want to wallop anybody with the brim or feathers. But just in case, be sure it’s strapped on securely.

Some folks really worry about blocking someone else’s view. While it can be a bummer to end up behind a whole bird’s worth of feathers, it’s pretty much par for the course (er... track.) Everyone behind you can just shift around.

(Don’t) Dig in Your Heels

Unlike the horses, Derby for you is a marathon, not a sprint. So we strongly advise against extra-high, super-sharp heels. Aside from your personal comfort, if you do any walking on grass, you’ll be sinking in.

If your inner fashionista would rather die than dishonor yourself with block heels, fiiiine. Just do yourself a favor and invest in clear heel caps; they hardly show up in photos and certainly look nicer than clods of dirt.

Dress Code

There are many instances where dress codes are considered flexible. Derby is not such a place (unless you own one of the horses running. Then it’s kind of a free-for-all.) Look up the dress codes before you go. The infield is a little more playful, but you should still show up and show out.

For Oaks, things are a smidge dressed down, though we fully recommend embracing the “pink” theme. Thurby is way more creative and colorful.

Earring Saviors

Ever lose an earring? If it’s going to happen anywhere, it’s going to happen at Derby – stiff breezes, wild hats and mayyyyybe a few drinks can mean fashion disaster. And anyway, you’re probably wearing some of your flashier pieces, right? We fully recommend specialty backs for your earrings. Not only can they help keep you from losing a soldier, but can also alleviate the weight of heavier earrings (your lobes will love you.)


Your clutch isn’t just for decoration. Build a mini emergency kit for all the potential pitfalls of the day. Depending on space, we recommend packing along hairspray, bobby pins, lipstick, a cell phone charging pack, a tampon, moleskin padding (for blisters), a little spare cash and baby wipes. Depending on the forecast, you might also want to bring a rain poncho, sunscreen and/or sunnies.

Learn About Betting

It’s your duty to bet during the Derby. While we’re not opposed to going with the horse with the prettiest silks, it would behoove (ha!) you to at least learn a little bit about how betting works. From trifectas to long odds, it’s important to know what the smartest bets are. Sure, bet on your favorite to win, but also make a bet that could net you some cash!

Be You!

Look, Derby is supposed to be fun. So have fun! Show your wild side (but don’t get crazy). •

Posted on 2023-04-01 by Amanda Harper