Kentucky Derby Fashion
What comes first? The hat or the dress? Fashion takes a center stage at the Kentucky Derby and there’s a lot that can go into planning your perfect outfit. For more information on Kentucky Derby trip planning, check out our post here.
So what’s the answer? In my opinion, 100% The. Dress.
I think the best part of Kentucky Derby outfit planning is finding a perfect dress and then planning the hat and all of the details that will go on it. So let’s get you started!
Kentucky Derby Dresses
While technically anything goes, for ideal Kentucky Derby fashion I encourage people to think more modest and southern belle like. Nothing too short or revealing. It’s a long day at the racetrack so you definitely want to be comfortable.
It always helps to get some inspiration for your dress. The Australian horse racing scene is the epicenter of horse racing fashion. “Fashions on the Field” is basically an Olympic sport down under and they are lightyears ahead of the United States. Here are some of my favorite Instagram accounts to get outfit ideas:
There is no one stop shop when it comes to Kentucky Derby dresses so it’s all up to your style and budget. You can find great dresses on Amazon or you can look at higher end designer options if that’s your thing. One site I like to recommend that also showcases typical race day looks is ChiChi London.
Fun Fact: I won a fashion contest with a dress, purse and accessories all from Amazon. Don’t feel like you have to break the bank to look nice!
🛒 Check out my favorite Amazon dress options 🛒
Kentucky Derby Hats
Kentucky Derby hats can run you anywhere from $25 for a simple fascinator to well over $1000 for custom made designs. Most Kentucky Derby hats will average around $300-$500. If you are on a budget, there are plenty of options on Amazon that you can wear as is or add to.
If you have the time upon arriving in Louisville, Dee’s Hats has tons of base hats to choose from. Additionally, if you bring in your dress they can help you choose additional décor and they can prepare it for you for an additional cost. The closer you get to Derby day, the less availability there may be for this so I’d recommend calling ahead to see if this is still an option. Many boutiques and even the malls in and around Louisville also have hats for sales if you need something last minute.
Overall, standard Kentucky Derby hats are becoming more difficult to find so if you want something unique you will likely need to look for a local milliner. If you go this route, you will need to plan for this well ahead of time as many stop taking orders prior to April if not earlier.
I make all of my own hats and fascinators so I do not have a go to shop or milliner I can personally recommend. I’d start by Googling Kentucky Derby Hats to see if you can find anything local and to get an idea of what you can find at your price point.
🛒 Amazon hat ideas to get you started 🛒
Kentucky Derby Shoes
Shoes are an important part when planning your Kentucky Derby fashion. While most women do wear heels to the track, it’s a very long day to be on your feet in super high heels. I do wear heels every year as painful as it can be at times and I have two tips to help save your feet.
Shoe Tip #1 – Bring flip flops (or flats).
Even if you have a shuttle service for drop off and pick up from your parking lot, the day involves a lot of walking. Walking to your seat, getting food and drinks and making bets are just the beginning. You may venture to see the horses in the paddock or wander over to see celebrities on the red carpet. Sometimes, even if my feet don’t hurt yet I will throw my flip flops on before a long walk. Not only do I save my feet for a bit but I can walk faster to get through the crowds quicker too.
Shoe Tip #2 – invest in the comfort brands.
Aerosoles, Lifestride, Naturalizer and Natural Soul are some good options. No, you aren’t stuck wearing short, ugly shoes, they have lots of good, fashionable options. Don’t make the mistake of finding a random brand of heels just because they are cheap. They may feel ok while trying them on but they will have zero support after the first 20 minutes.
🛒 Comfortable shoe options that can be found on Amazon 🛒
Purses and Handbags
Churchill Downs does have rules around the size of bags you can bring in so always check their website first. While a matching handbag is not necessary it definitely pulls your look together and has become an essential piece in my Kentucky Derby fashion.
I normally try to find something unique that can fit my phone, lipstick, and small wallet. My recommendation for a handbag is the same as a dress. You can find nice options on Amazon or look for something higher end if that is your style.
One thing I would consider is where your seats are. If you do not have covered seats and it is forecasted to be a rainy day, leave the designer bags at home. The racetrack gets very dirty as it is and throw in rain and 150,000+ people and it’s not the cleanliest place.
🛒 Get inspired with these hand bags and accessories 🛒
Rainy Day Outfit Tips
Rainy weather is common on Kentucky Derby weekend. You can NOT bring umbrellas into Churchill Downs. You will be limited to a rain coat and/or ponchos. This is all about hoping the meteorologists have the hourly predictions right and making the best decision you can that morning.
We bring many ponchos on rainy years as 1 will not cut it. It’s nice to have extra to sit on, cover your legs and feet and to cover your hat! If it’s pouring all day you will generally leave your seats between races as there are under cover areas you can wait in and your seat will always be wet. Buy ponchos before you get to Louisville if you can. If they forecast a rainy Derby, it can be hard to find them.
Fashion Tip: Try a snazzy clear raincoat so you can still show off your outfit! I used this one last year (it rained…the entire day) and it held up well.
For the years that predict rain, you can either tough it out with soaked heels or, you can bring rain boots with the possibility the rain leaves and you are stuck carrying boots around the rest of the day. I’ve recently invested in more comfortable rain booties so they aren’t as large to carry around. I would not recommend leaving your boots at your seat (unless you are ok if they get stolen). It’s tough to say who you have sitting around you and if they will turn into a thief while you are away.
Kentucky Oaks
If you are attending the Kentucky Oaks (the Friday prior to Derby Saturday) everything in this article still applies but please make sure to wear pink!
Kentucky Oaks days is essentially “ladies day,” if you will, as the feature race of the day is for 3 year old fillies. Think of it as the Kentucky Derby for girls even though a filly could run in the Derby – we won’t get into the details.
The Kentucky Oaks also partners with Susan G Komen for Breast Cancer awareness and includes a Survivors Parade that is a fan favorite. Wear pink to support this cause!
Kentucky Derby Infield Attire
If your seats are in the Infield, everything is much more casual and you can ditch the heels. A casual summer dress is fine or you can still get as fancy as you want! The entire area is grass and unless you bring a chair there is no specific seating areas so be mindful of your footwear.
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