What to Wear to the Kentucky Derby: The Ultimate Guide
The most wonderful day in the 502 — the Kentucky Derby — is on its way. And while the horses are beautiful, athletic, money-making powerhouses for their owners (and lucky betters), any versed Louisvillian knows the main attraction of this iconic event is the fashion. But knowing what to wear to the Kentucky Derby can be confusing!
And maybe the prospect of making a spontaneous fortune is also slightly interesting to us as well, but where most of us will never be rich enough to afford a stable full of prize-winning thoroughbreds, we can all manage to serve a stunning Derby Look™.
While there is no strict dress code, there are certain dress standards for different areas of Churchill Downs, so be sure to look that over. But with our help, your gaudy getup will be grabbing the eyes of dazzled admirers and not getting you kicked out of the Turf Club boxes.
Psst: Coming to Louisville for the Derby? These other posts will help you plan your trip:
- What to Wear to the Kentucky Derby: The Ultimate Guide
- Kentucky Derby Tips: The Ultimate First-Timer’s Derby Guide (by a local)
- Louisville Weekend Trip: The Perfect 3-Day Itinerary
2023 Kentucky Derby Tickets & Parking Passes
Need to pick up a ticket for Derby, the Oaks, Thurby, or Dawn at the Downs, or a parking pass for Churchill Downs?
Before you pay full price, we highly recommend looking on VividSeats and StubHub, where you can usually find reduced price tickets, single-day tickets, and even parking passes to help you save money (so you can spend more on betting and mint juleps, obviously)!
What to Wear to the Kentucky Derby
So, let’s start with the basics. When you think, “Kentucky Derby fashion,” picture what you might wear on Easter Sunday — if that was the category of a runway challenge on RuPaul’s Drag Race.
We’re talking big, bodacious hats with flowers, creamy pastel colors, seersucker suits, and loud accessories. It’s basically a garish fashion festival where men and women alike try to one-up each other in a blatant display of wealth and (often poor) taste.
So, if Derby isn’t drag for the wealthy, we don’t know what is! That’s why we’re helping you touch the fashion and change your life with a little history and a lot of suggestions on what to wear to this year’s Kentucky Derby.
- Pssst: We also have a Derby first-timer’s guide, if you need some help figuring out how to do Derby as well!
History of Kentucky Derby Fashion
The first Kentucky Derby began during a time period when women were still wearing corsets during their daily lives, and with nearly 150 years of racing, Churchill Downs has seen its fair share of fashion trends come and go — from daring flapper looks to the emergence of the mini skirt (gasp!). There was even a brief trend in the 1910s of “hobble skirts,” which severely limited its wearer’s stride, but served a gorgeous silhouette.
Though the first Kentucky Derby ran in 1875, it wasn’t yet the fashion event of the year that we now know and love. Col. Meriwether Lewis Clark Jr. (yes, the grandson of THEE William Clark of the Lewis and Clark Expedition) wanted to establish a ritzy horseracing venue in Louisville akin to what audiences in Europe enjoyed at the time. This RuPaul’s Drag Race UK runway category was literally “Off To The Races,” if you’re looking for some more inspiration from across the pond.
The only hitch? Local women were hesitant to participate, possibly due to the gambling and drinking associated with horseracing events. It wasn’t until Col. Meriwether Lewis Clark Jr. and his wife had the bright idea to pitch the races as social outings for ladies, where they would be required to wear “full morning dress,” aka, fully formal clothing that is worn before 6 p.m.
And believe it or not, the flamboyant headwear that’s associated with the Kentucky Derby nowadays didn’t really become trendy until the 1960s, when social fashion norms began to shift — and women wanted to stand out from the crowd. Nonetheless, hats were an important indicator of social status, so you still saw aristocratic women at the track wearing wide-brimmed hats adorned with feathers in the late 1800s to early 1900s.
Contemporary Kentucky Derby outfits get a little more room to roam, and in my estimation, the campier the outfit, the better. I’ve still yet to see someone rock a piece like what Kim Petras wore for the 2021 “American Fashion” MET Gala, but I feel like this could be the year we get close. It’s floral, colorful, and the focal point of the whole look is a giant horse head — you can’t get more Kentucky Derby fabulous than that.
My personal preferences aside, there are no real rules when it comes to dressing for Derby Day — again, unless you’re in a specific area — because it’s important to dress for where you’ll be spending the day, according to Churchill Downs. While people with seats in the grandstand or clubhouse might wear an understated spring dress and heels or a linen suit, someone in the infield may opt for a suit with shorts or a two-piece cropped dress. I was today years old when I learned crop tops aren’t allowed in the business casual areas of the Downs, boo.
Regardless, you’ll want to dress to impress as this internationally-renowned event attracts a host of celebrities each year, with appearances from Queen Elizabeth II (RIP), Michael Jordan, Kim Kardashian, and more over the years.
Hats at the Kentucky Derby
Despite what I said before, there actually is one rule of Kentucky Derby dressing. You have to wear a hat.
No, you won’t be escorted out from Churchill Downs if you’re not wearing a hat. But, it’s a fun way to spice up your look and show people what you’re all about on the big day. Plus, wearing a hat to the track is considered good luck, and you want the odds in your favor if you’re trying to win some bets.
Our hard and fast rule on what dictates a Derby hat? If it sits on your head and you’re at the Derby, it’s a Derby hat. That’s it. Though the trend began with women, both men and women participate in the tradition these days, whether they break out the glue guns and glitter to craft their own, or they contract a local milliner to craft a stunning, one-of-a-kind piece.
Generally, you’ll see women wearing colorful, wide-brimmed, Southern Belle-esque hats adorned with flowers, ribbons, and sometimes small icons like butterflies, which have been popular in the last few years. Men often go for smaller, less flashy hats like fedoras.
But we love people who dare to be different with their Kentucky Derby outfits, and it’s no shock to see attendees — regardless of gender — arrive wearing horses on their heads, money glued to their hats, and other eccentricities that delight us and make the event worth attending.
Simple or extraordinary, you aren’t really at Derby if you aren’t wearing something on your head, and much like the tickets themselves, Derby hats can range anywhere from pre-made and inexpensive to milliner-made and costly.
Where to buy Kentucky Derby Hats for women
You can find Derby hats and fascinators online for budget-friendly prices, even on Amazon. There are also plenty of places right here in town to pick up a hat! Below are a few of our favorite picks:
- If you’re in a pinch or just want to be extra creative, get out your hot glue gun and make your own! Start with a wide-brimmed sun hat that you can find at any store, like this from Amazon. And then follow a tutorial like this! Remember, you will always earn extra points (in the form of strangers complimenting you) for creativity. The sky is the limit, truly, and you’ll have fun pretending you’re in a design challenge on RuPaul’s Drag Race.
- For more unique options, you can always find a one-of-a-kind design on Etsy. There’s plenty to inspire your outfit, from stunning butterfly fascinators to fuchsia and teal designs.
- If your budget allows, there are lots of local places in Louisville to get Derby hats while supporting local artists and craftspeople! Start by looking into the Featured Milliners picked each year by Churchill Downs, such as Formé Millinery.
- Other local hat shops to find your perfect Derby hat include The Mysterious Rack, HeadCandi, Work the Metal, and Dee’s Hats — there are a ton of shops in town that sell Derby hats!
- See also: Tiffany Woodard Designs. She’s another locally-based milliner and we’re obsessed with her Giant Dandelion Fascinator. It’s beautiful, delicate, and unique from most of the other floral designs you’ll find out there.
- Browse The Mad Hatter’s collection online for something big, bold, and feathery. Keep up with her Instagram for updates and more Derby outfit inspiration.
- The Hat Girls, based in St. Matthews, is online only except for the month of April. In addition to its dynamic offering of hats and fascinators, you can also have a custom hat made.
Where to Buy Kentucky Derby Hats for Men
Did you know: men have their very own “derby” hat? Yup. It’s the bowler hat — also called a “derby” — which became common headgear at horse racing events in the late 1800s because it was hard for them to blow off spectators’ heads. Here are a few places to get your own derby, or another style of men’s hat:
- Why not go classic Derby with a bowler hat? This smart hat will say that your classic, stylish, and know your derby history. Plus it comes in plenty of colors to match your Derby look!
- Channel your inner Crocodile Dundee with this crushable wool hat. It offers cowboy charisma with its belt and feather and reminds us of one of the cool hats Chris Stapleton might wear.
- Don’t turn your nose up at this straw fedora. Straw hats in this style are pretty common on race day, and pair well with seersucker and linen suits. Plus them come in all kinds of fun colors!
- This wide-brim fedora panama hat is sleek and handsome, and will keep the sun off your face on race day (please don’t let it rain!!!). Plus there are lots of colors for this one, from shocking orange and lime green to more subdued shades.
- Why not make a statement with a smaller hat like a straw pork pie? It’s not only adorable and stylish but has lots of classy colors to match your Derby day finery.
Kentucky Derby Attire for Women
If it wasn’t clear from the section above, the hats are the real star here, but clothes that team with the theme of your hat are also important, too.
There are no “official” colors for the Kentucky Derby, but you’re likely to see a lot of pink outfits on Oaks Day, which is also known as ‘Ladies Day,’ and happens the Friday before the Kentucky Derby itself.
All the three-year-old fillies race on this day, and Churchill Downs asks attendees to incorporate pink into their outfits to drive attention to the fight against breast and ovarian cancer. Bonus: Churchill Downs also hosts its Survivors Parade on Oaks Day, honoring breast and ovarian cancer survivors.
Different shades of red are more prominently featured in the various outfits on Derby Day, as the race is also referred to as the “Run for the Roses.” So, you’re bound to see race day fashionistas emulating this symbol of the Derby in their dresses, hats, handkerchiefs, and other accessories, like this rose-shaped clutch purse.
Nonetheless, women from around the country — and the world — arrive in mint green, orange, turquoise, yellow, and chic black-and-white outfits. So, while you should keep that Easter Sunday color palette that we mentioned in mind, you don’t have to stick squarely to that if you’re being called to a gorgeous royal purple or a deep, mystical blue.
In terms of dresses, think floral prints (For spring? Groundbreaking) and cocktail dresses with seasonal heels or sandals. A flat shoe option will also be your friend if you have a lot of standing or walking ahead of you inside the Downs, and many women opt to bring a cheap pair of flip flops to the Downs as well.
But please, you are a modern Southern belle, which is why I’m here to tell you that you are too sexy for ballet flats. There is no reason those shoes should have made it out of the 2000s, and I will not allow them to make a comeback. Please don’t wear them.
Instead, opt for something with a trendy shape or some kind of eye-catching detail, like these pointed toe flats or these strappy flats. And a little bonus option for you because I love shoes, these Mary Jane-style flats would also be cute, but check the weather before you opt for velvet — few things are as upsetting as waterlogged velvet or suede.
Where to buy a Dress for the Kentucky Derby
With a little stylish imagination, you can make any dress a dress fit for the Kentucky Derby.
Generally, people who go for a big, wild hat wear a more understated dress while people who choose the bold dress wear a more understated hat. But by all means, as your maximalist friend, I encourage you to go all out on both if that’s what your heart says. Here are a few dresses to inspire your Derby Day outfit.
- This wrap maxi dress is what we’re talkin’ about. This dress has a delicate floral print, movement, and it feels fancy enough to wear into the business casual areas while still fitting in elsewhere at the Downs.
- Some women go really classic with their dresses, so this 1950s retro vintage cocktail dress is a loving nod to y’all. I’m in love with the bold ochre color (though there are plenty of color and pattern choices!), the darling cap sleeve, and heart-shaped neckline. It’s a retro dream.
- The baby doll dress is one of my favorite trends of the last year because it’s so cute and feminine. This dress is no exception, and it comes embellished with pearls. Since it’s relatively simple, it’d be pretty easy to make or buy a hat to match.
- Something about a long pleated skirt like this breathes elegance to me, and this dress is one I can envision sitting in Millionaire’s Row. The colors are refined and the irregular hem of the skirt gives it some whimsy. Definitely a good base for your Derby day look!
- This flowy yet fitted dress and is easy to picture with a big feathered hat or fascinator on top and it comes in 10+ patterns and colors. It definitely serves “1930s glamour” and I could easily see Jean Harlow or some other star of old Hollywood rocking this out!
- Show off your shape with this bodycon dress that comes in 10 different colors. With a sleek fit and daring ruffle you can show some body-ody-ody on race day and be the belle of the ball, er, race!
Where to buy Kentucky Derby Accessories for Women
While accessories might play a smaller role in your overall Derby look, to borrow an old theater adage, there are no small parts, only small actors. Check out these fun, Derby-themed accessories to elevate your look, they can play whatever role you’re looking to fill.
- You’re a winner, baby. Which is why you deserve to don some winning, white thoroughbred earrings donning the iconic garland of roses! White not your thing? Check out these super adorable pink horse earrings instead.
- Don’t have your ears pierced? Try these beautifully beaded horseshoe and rose clip ons that will certainly bring you luck on raceday!
- Derby is just not Derby without the Mint Juleps. These earrings make it so that you can wear this iconic beverage without having to drink one, but I mean, you should totally drink one for me! This shop also has a lot of other gorgeous Derby earrings.
- If you love the colors and pageantry of the jockey’s jerseys, check out these yellow and orange jockey jersey earrings that say “KY” on them. Now that’s onbrand!
- For a simple rose motif, check out these earrings and matching necklace to match. You’ll basically be a rose garland on race day, and that’s really the goal, isn’t it?
- Embrace the nearly 150 years of horseracing tradition at the Downs with this colorful jockey on a race horse brooch that will look amazing on your dress, hat, or purse!
- This classy clutch with a golden horse on the front is available in black and white to add a pop of elegance to your look, especially if you match the woodsy print on the inside. Perfect for the woman with style!
- These are roses you won’t have to run for. This silky soft fabric rose clutch will keep your valuables safe and it’s small enough that it doesn’t violate Churchill Downs’ bag policy.
- If you want to be in the money when it comes to placing bets at the racetrack, check out this crystallized stack of cash clutch. You can bet on being super stylish and maybe even winning some money!
Kentucky Derby Attire for Men
For suits, you’ll want at least a suit jacket even if you’re sporting shorts. Seersucker, cotton, and linen are all common fabrics among Derbygoers for breathability, and so are suits with crazy patterns.
You may not expect it, but men’s suit jackets can be just as eye-catching as the women’s fashion. One trend that’s particularly cute to see is the prevalence of matching couples: either the lovebirds are sharing a color palette or the same bold print across both their outfits.
Where to buy a Suit for the Kentucky Derby
If you’re a man and you’ve been reading this long, now is your time to shine. Here are a few options to inspire your Derby day outfits:
- To kick this section off, let’s start with the classic linen suit. This two-piece is available in 10+ colors and serves as a gentle introduction to men’s Derby fashion.
- Let’s turn it up a notch. This floral suit is a marriage of loud print and floral, masculine elegance, which, let’s be real, is something we definitely want to see on race day!
- Roses aren’t just for the ladies. This black tuxedo jacket features shimmering rose detail and a single-button closure. This is a super easy jacket to style and match your significant other!
- Live out your partner’s Hugh Dancy fantasy when you wear this dashing two-piece suit, with tuxedo vest and pants. Because honestly, who is more handsome than Hugh Dancy? Maybe you, in this suit.
- Though this section is mostly about suits, you’ll also see a decent amount of men just wearing a nice shirt and pants. It can really be that simple. Go the extra mile and make that nice shirt a bold, floral print.
- Similar to our retro outfit for women, if you’re looking for a throwback-worthy fit, try this checked vintage suit. Remember, Derby fashion can be somewhat out there, so don’t be afraid to stand out!
Where to buy Kentucky Derby Accessories for Men
Before we launch into men’s accessories, keep this list of prohibited items in mind when you’re thinking of fun ways to dress up your look. While we love to make a statement with our outfits, we can’t do that if Churchill Downs won’t let us in because we have something we shouldn’t.
- Ties are a man’s best friend….or was that dogs? Anyway, this adorable pink tie has horses on it and will make you look so dapper. Need I say more?
- Maybe the look you’re going for would be complete with LED light-up suspenders and bow tie? I mean, what would be more fun and flashy in the infield? Even if it’s not your jam, you’re welcome for letting us help you find it.
- Paisley is one of those patterns that I wish had never gone out of style. It’s so fun and groovy, and this paisley bow tie and matching handkerchief easily embody the playful spirit of Derby Day.
- If your style is more understated and you want just a gentle pop of color, try one of these floral ties. They’re a perfect dose of color for a classic suit look.
- One more floral tie and then I’ll stop, I promise. These skinny ties come in a wide variety of botanical motifs, are made of cotton, and come with a special gift box, according to Amazon.
- If you opted for a plain suit or nice shirt, this cloth rose lapel pin can add a little more Derby Day flair to your look. Plus, there’s two, in case you want to pin the second one on your date (you know we love a matchy-matchy moment).
- Pair one of those tan linen suits from the section above with a hat and these sunglasses and your look is as good to go as the horses at the starting line.
- This retro skeleton watch with diamond detailing is just plain cool, and even though it has a lot going on, it won’t steal your suit’s thunder.
- Few things complete a look like a belt, and this one comes in 12 colors — so you can match to your suit or have an unexpected pop of color.
How to Dress for the Weather
The Kentucky Derby is sometimes a gorgeous day… And sometimes a cold rainy mess. That’s Kentucky for ya! Keep these tips in mind when planning:
- Pack a clear rain poncho or fabulous raincoat, because view-blocking umbrellas are not permitted at Churchill Downs — even clear umbrellas.
- Ladies, consider packing a spare pair of flip flops or flats to give your feet a rest after a long day of running back and forth between your seat, the restroom, and concessions. Your feet will thank you on the long walk back to your car at the end of the day.
- Always check the weather in the days — and even hours — leading up to the event, as the weather can change on a dime and leave you woefully ill-prepared, which seems to be the case with nearly every Derby ever!
So do you know what to wear to the Kentucky Derby now? What questions can we answer? Drop us a comment below!
Psst: Coming to Louisville for the Derby? These other posts will help you plan your trip:
- Kentucky Derby Tips: The Ultimate First-Timer’s Derby Guide
- The Best Hotels Near Churchill Downs & Where to Stay for the Kentucky Derby
- Louisville Weekend Trip: The Perfect 3-Day Itinerary
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