a blog for everyone and their mothers

Kentucky Derby Tips & Tricks


How to Navigate the Kentucky Derby @popcosmo.com “Derby” in Louisville is not just a day… it’s an experience. It lasts a few weeks and there are more events leading up to the Kentucky Derby that we can list here. Our first year in Louisville, we were surprised, amazed, and overwhelmed with the parties, events, balloons, fireworks and airshows. There are official events for the Kentucky Derby and plenty of unofficial ones.

My first year at Derby, I had a million questions and asked a million + 1 people for advice. Over the years, I questioned even more patient people about their tips and tricks for “doing Derby” and below is the advice I've gained from them + my experiences. Mastering the art of the Kentucky Derby is do-able, with a few tips & tricks.

If YOU have any tips you’d like to share, please do so in the comments.

The most asked question: what do I wear to the races?:

  • The bigger the better, the louder the better, the brighter the better! But comfort is key and so is something washable since the likelihood of a drink splashing on you is high due to hours spent around drinks and total number of drinks you will encounter throughout the day (regardless of whether or not you will be drinking). Add the fact that you might be eating a picnic lunch on your lap if you are sitting in an outdoor box seat, and you have a recipe for a messy day.
  • Prints and washable dresses are all good options, silk is best left for the jockeys, and warm weather fabrics are a must.
  • You are only allowed to bring in 12” bags this year, so we recommend a crossbody bag (you’ll want free hands).
  • You have long days ahead of you with lots of walking involved, so stick a pair of the most comfortable and blister-free flats Yosi Samra fold-up shoes or a pair of flip-flops in your bag (your feet will thank us) and you’ll look like you’ve been doing Derby for years. If you can’t bear to change, wear broken-in comfortable shoes, and bring bandaids.
  • Bring ponchos if there's an inkling of rain since you can't bring an umbrella. If you wear a clear one, your outfit will shine through. Check the weather before you go!!
  • Don't over-accessorize. If you have a flashy hat- keep your jewelry in check. Conservative hat- play up jewelry.
  • Do not try to get a spray tan a few days before Derby. You'll be waiting in line for hours.
  • Here's a post about what to wear to the Kentucky Derby.

On Fridays we wear pink: Oak’s Day is Friday and is the filly’s race. It is just as exciting as the Kentucky Derby. Schools cancel classes and it had been local’s day, but now it is no longer a Louisville secret and is getting to be just as crowded and festive as Derby Day. "Locals day" is being pushed back to Thursday as more people arrive for the weekend to celebrate. In the past few years, the tradition had been to wear pink to honor breast cancer research and survivors. You can get decked out in all pink (check  out a Oak's Day outfit idea) or wear touches of pink… and don’t think pink is just for the girls! Guys can sport a pink tie or dress in all pink too. Vineyard Vines has a fabulous men's Derby collections.

Fascinator v. Big hats: Obviously, personal preference. I'm a fascinator girl -- something about being able to turn my head and peripheral vision (go figure). But, if you’re sitting outdoors and the day is sunny, a big hat could come in handy. Regardless, bring sunscreen!! Whatever you wear, make sure it doesn’t pinch, or slip. If you forgot to bring a hat, run by Dee's and they'll make one for you to match your outfit.

Calling all party girls: If you can party all day and party all night and want to support charities, purchase tickets to the Julep Ball and the Barnstable Brown party and mingle with celebs who show up for Derby and Oaks.

Dawn at the Downs: Eat breakfast on Millionaire’s Row and watch Derby contenders working out. It’s a unique Kentucky Derby experience on the weekdays.

Can we get there from here?: Plan on spending a long time in the car and consider it part of the experience. Unless you arrive very early in the morning, and even if you do, you might be parking in someone’s yard, so bring cash. Unless you park at Churchill Downs, plan on a long walk to the track, and check out these parking maps for Derby week in advance.

Some options to avoid parking by Churchill Downs (which can be a nightmare): park near one of the many bus stops and bus into Churchill Downs, park in the lot near Cardinal Stadium, find a teenager to pick you up and drop you off, or rent a bus for a big group, or take Uber, which arrived this year.

Food, food and more food: At the track – If food is not included with your ticket, you can bring a box lunch, but be sure to check the rules about what is allowed to be brought in the gates.

  • Vendors come around with drinks- order several. That way you don't have to wait in long lines, and next time they pass, you will be ready for another.
  • Remember to hydrate with water too!

Around Town – Make reservations for hotels and dinners (before and after races) as soon as you know you’ll be attending. Good luck finding either at the last minute. But, if you don’t have reservations, find a Louisville food truck. {We love Grind burgers!} And since many homeowners head out-of-town for the Derby and rent their houses, you might find one on VRBO.com or airbnb.com at the last minute.

It's Bourbon country, baby!: As the home of Bourbon, get ready to drink a lot of it at the Derby (but please don't drink & drive!). And while here, visit the distilleries, which can even be family outings. Actually the official drink of the Oaks is the Oaks Lily which is made with vodka; but yes, the traditional drink of Churchill Downs and the Kentucky Derby is a Mint Julep, which is made with bourbon. Although traditionally served in a silver cup, at the Derby (and Oaks), you’ll receive a commemorative glass cup with each order. Keep ‘em and start your collection.

Tickets & Seating: We suggest buying tickets directly from Churchill Downs. You’ll get a good description of your seat and the amenities. Pay attention to where your seat is located - your box seat may be in a section exposed to rain or sun all day long. If you want to play it safe, make sure you buy a “covered” seat. If you are trackside, you are not covered, but you’ll have a great view. Your seats (unless you are in suites indoors) are folding chairs. There are six in a box and your “box” is actually a metal bar, so you’ll know your neighbors quite well by the end of the day. The fun of Derby is seeing the outfits, the horses before the races, the horses walking to and from the Paddock, etc., so wandering around is not only highly encouraged, it is part of the experience.

The Ladies Room: No matter where you sit, you will have a great view. But the bathrooms are what set everyone apart. Drinking all day means... long lines in the ladies' room. But don’t be discouraged. The efficiency of the attendants is the best I’ve ever encountered. However, if you are headed to the infield, byot. (Bring your own toilet paper). We hear they've been known to run out. If you are in the suites, enjoy the semi-privacy and no long lines!

What is the Infield?: No tickets? No worries! You can always gain access to the infield. While Oaks Day may not be that crowded, Derby day will most definitely be packed. The infield is made up of a partying crowd that’s come to enjoy themselves. You’ll have access to the Paddock area as well, but since there is no limit to the number of tickets that are sold for the infield, prepare for crowds. And if it has rained, get ready for mud. And unless you secure a spot near the track, you might miss the races, but you can enjoy the party!

All bets are on!: If you aren’t an expert in betting, read the program. There is a little tutorial and key in the front. You don’t want to be  “that” girl holding up the line, you want to be talking about trifectas with the rest of the gang.

  • Bring $1 bills. Lots of them… the lines to the ATM are longer than the betting lines.
  • If you win, it's customary to tip the clerk. (Supposedly it brings you good luck!)
  • Betting on colors, names and birthdays is fine. You'd be surprised how many people beat the odds with these bets - but don't hold us to it.


  • Bring a phone phone for photos and a backup battery because service is spotty, especially if you want to Instagram.
  • Show Louisville some love with the Louisville Love app for photos, if you have service!
  • Bring ibuprofen or aspirin. With noise, hats, cigar smoke, heat, etc., you have the perfect storm for headaches.
  • Fashion First Aid has a handy pack you can carry in your purse of essentials you might need for the day. We kinda think it would be handy for trips too! It'll cover hat problems, heel blisters, armpit stains and more in a handy package. (I'm pretty impressed by how they have a solution for just about any problem I have!)

After you've completed all your planning for the best weekend ever, the most important tip is to sit back, enjoy the races, and have some fun in Louisville! It's a fantastic city to explore apart from the races with amazing dining, wonderful parks, a beautiful river, and the friendliest people you ever did meet.

Many thanks to local friends Natalie, Ashley, Christy of The Bourbon Blush, and Shelley for their tips, & everyone else I've pestered over the years!