In 2023, fashion will once again take center stage for men and women at the Kentucky Derby.
Of course, we all come to historic Churchill Downs to watch the Thoroughbreds race, but make no mistake, watching the game goes hand in hand with day at the track.
Here’s a quick list of what to wear and what not to wear Kentucky Derby weekend in Louisville.
What kind of hat should I wear to the Kentucky Derby?
Hats aren’t technically required at the Kentucky Derby and Kentucky Oaks, but they might as well be. Most Derby fans attend races with some type of head gear.
While men don’t have as many style options as women, a lightweight bowler or straw hat is still popular and fashionable.
In the ladies, you’ll see a bit of everything in horse racing, from the elegant to the extravagant. Most seasoned Kentucky Derby fans have chosen a style that best matches the section where they have tickets.
If you’re sitting indoors on Millionaires Row, a tall brim or sleek fascinator are great choices. That’s because you don’t have to worry about the rain ruining your investment (yes, Kentucky Derby hats are expensive) or the wind blowing it away.
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In other “less dressy” places, smaller fascinators might be a better bet. Wherever you sit, keep in mind that you’ll be wearing the headset throughout a really long day, so make sure it’s as comfortable as it is stylish.
As we mentioned, hats can be expensive and cost hundreds of dollars, but there’s nothing wrong with swapping hats with friends and family. Trust us, if you’re having a good time, no one will remember who wore which hat last year. You can also make one yourself. Dee’s Crafts in St. Matthews is a great place to start or you can scroll through ideas on Pinterest around Kentucky Derby time for inspiration.
Pro tip: You can easily clean last year’s sweat-soaked interior tape with a toothbrush and some Woolite. You can also clean dirt and stains from a straw hat.
What kind of outfit should I wear to the Kentucky Derby?
The Kentucky Derby is a fashion show. You’ll see women in everything from spring dresses to tailored suits. This varies depending on where you are seated, so take a look at your ticket and make sure the outfit you choose will be appropriate. (i.e. you’ll miss stilettos in the infield – or anywhere, really. It’s a long day on your feet, ladies!)
Guys tend to “go all out” in lightweight sports jackets and pants. They can opt for preppy Bermuda shorts and a sports jacket in the infield and absolutely everyone wears sunglasses. Sensational ties are the easiest way to make your Kentucky Derby outfit as unique as you are, whether it’s a luxurious traditional silk tie or a Southern-inspired bow tie.
Plus, this event takes place in the spring, so consider pastels for your outfit to capture Instagram-worthy photos on the red carpet.
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A word of warning, ladies. While you’ll see fashionable jumpsuits and rompers at every turn, is that really what you want to struggle with in a public restroom where the queue can last 15 minutes or more?
Pro tip: Try renting the runway for a designer dress that you don’t have to spend a month’s rent to buy. You get the dress (and/or accessories) for four days and have to return it, but it’s worth it. Insurance is included, just in case you get stuck in a muddy situation.
Is there a dress code at Churchill Downs for the Kentucky Derby?
Yes. There is an official dress code in certain areas of Churchill Downs, depending on where you purchased tickets.
If you’re a beginner, make sure you understand your seating environment. Are you in the air-conditioned comfort of Millionaires Row? On an element-proof picnic blanket in the infield? In a covered clubhouse box… or not covered? If you don’t know, find out and dress accordingly.
Here is a brief breakdown of the different dress codes in the suites seated on the track:
business casual (i.e. shirts with collars for guys; no denim, sneakers, or “inappropriate” clothing) is required in the Turf Club, Trophy Room, and Millionaire Row, where you can split your time between air-conditioned dining rooms and outdoor terraces, some of which are covered. Guys, a jacket is required in the Derby Room and The Mansion.
The Churchill Downs website details what is appropriate in each section of the track, as well as several areas where “worn or ripped clothes, halter tops, sportswear, frayed or ripped jeans and belly tops are considered inappropriate clothing”.
If you have tickets to the clubhouse or grandstand seats (which are also reserved), casual dress is permitted, although you’re unlikely to see any of that.
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And if you’re in the infield, there’s no dress code, but a lot of people dress up. Remember you will be walking a ton and sitting on grass…or mud. So if you insist on heels, they should be practical wedges and not high heels. Or skip them altogether for cute sandals or ballet flats. There are even flats that fold up, which could be useful if you can fit them in your bag.
In fact, no matter how fashionably dressed you are, most women bring a pair of flip flops to get back to the car at the end of the errands. There’s no shame in that.
Pro tip: If it’s raining, get some cute rain boots to match your outfit. Be sure to pack a poncho, as umbrellas are not permitted on the trail.
What are some other fashion tips for the Kentucky Derby?
First, don’t forget to bring sunscreen. If the weather is nice, you will burn yourself. You’re out for nearly 12 hours, after all. Sunscreen is smart, even under your makeup, ladies and gentlemen.
Second, invest in a makeup fixer. It’s ideal for women who don’t want to mess up the makeup they applied in the wee hours of the morning. It will keep your makeup looking fresh for hours – ideal for those who sweat or are worried about mascara smudges in the rain.
Third, reduce your purse. Trust us, you don’t want to juggle a gigantic bag with your mint julep and running schedule. Installation restrictions prohibit purses taller than 12 inches in any direction.
The small size of the handbag allows you to carry only the essentials (vest, sunscreen, flip-flops, lipstick, glasses case, etc.)
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Fourth, be prepared for any type of weather. You really never know what the weather will be like in Kentucky in early May, so dress for whatever Mother Nature can throw at you – hail, rain, humidity or freezing temperatures. A cardigan or scarf is ideal for your shoulders, for the cold or to cover sunburned skin.
You are not allowed to carry an umbrella, so pack a light poncho for those unexpected showers. It doesn’t take up much space and you can use it to cover wet seats.
Pro Tip: Keep a close eye on the weather forecast until the moment you hit the trail. If you’re traveling to Louisville from out of town, come prepared with outfits you can layer — just in case.
What items should I not wear to the Kentucky Derby?
Pumps. We can’t stress this fashion tip enough. If you must have these babies for a little extra height, we suggest throwing them away just for the first shots and then leaving them at home. Consider something a little lower with more surface area and less chance of getting caught between cobblestones. If you like heels, try a chunky version that offers stability and style.
Avoid jeans or sneakers. You can technically wear them in the infield, but sandals, loafers, flats, or driving loafers are all better low-key options.
Ladies, skip your shapewear. Although they may be standard clothing for these sorts of dressy events, if it’s hot, you might want to reconsider. Try a looser dress for the often uncomfortable Kentucky Derby Day.
Contact Kirby Adams at kadams@courier-journal.com or Twitter @kirbylouisville.