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Derby Day Fashion Tips

April 13th, 2017

Fashion Tips For the Kentucky Derby & Derby Day Party Outfits

The Kentucky Derby isn't just about the horses. Derby Day traditions also include shining a spotlight on spring fashion. If you're one of the 150,000 people going to Derby, you want to make sure you dress the part.

Although there's only an official Kentucky Derby dress code for the premium seating areas, if you leave out a few accessories or choose certain styles over another, you'll stand out in the crowd — and not necessarily in a good way. Whether you're attending a Derby party, hosting your own Derby Day party or going to the big event itself, we've put together a guide to help you choose the best Derby Day outfits for women, men and kids.

Derby Day: Women's Fashion

Derby Day dressing for women is really a head-to-toe affair. If you usually follow a "less is more" rulebook when getting dressed, you're going to want to toss that rulebook out the window for the day. Coco Chanel's advice to "take one accessory off" before leaving the house doesn't fly here, either. Here's what you need to create a pulled-together, get-noticed-in-a-good way Derby Day outfit:

1. The Hat

Hands down, the most important thing you will put on to go to a Derby Day party or to Derby itself is a hat. We're not talking a baseball cap here, or even a simple cloche or fedora.

At Derby, hats are everything. You will stick out like a sore thumb if you show up bare-headed. Although it's not officially against the rules not to wear a hat these days, back in the day, if a woman appeared sans hat, she'd be considered indecent.

Despite the insistence on hats that dates to early days of the race, the hats worn at Derby weren't always the show-stoppers they are today. In the 1940s and 1950s, women wore modest hats that coordinated well with the conservative suits they wore to the event.

It wasn't until the 1960s that hat culture really took off. The width of the hats got wider, and the decorations and ornamentation got more elaborate.

Today, the type of hat a woman is likely to wear at Derby depends in large part on where she's sitting. The hats women wear in the general admission area tend toward eccentricity, while those ticket holders wear in the seated areas are a bit more elegant and refined.


If you're hosting a Derby Day party, don't be afraid to go all out with your hat. You can even host a hat-making event in the weeks leading up to the event, unleashing your creativity and ultimately creating a gorgeous piece of wearable art.

A newer trend on view at Derby in recent years is the fascinator. We have the Duchess of Cambridge to thank for this trend. A fascinator is sort of like a mini-hat. It's usually a flat disc that is covered with feathers, gems and lace. It's not quite a hat, because it doesn't have a brim and won't do anything to keep the sun out of your eyes.

While a hat covers your entire head, a fascinator is usually secured to one part of your hair using a clip or a comb. It's more a decoration that is meant to work with your hairstyle than something meant to conceal your hair. If you prefer to make a statement on a smaller scale, a fascinator might be the best pick for you.

2. The Dress - Derby Day Dresses

If you're sitting in a premium area at Derby, you'll be expected to wear a dress. Women sitting in general admission areas or attending a party elsewhere don't necessarily have to wear a dress, but it is encouraged. It's all part of the spirit of Derby Day fashion.

Dresses are usually a bit understated at Derby, since so many women go all out when it comes to their hat. You don't want to have a loud and eccentric hat and a loud and eccentric dress. The entire look would just scream "too much!”

Really, when it comes to your Derby Day dress, you can't go wrong with a solid-colored sheath or fit-and-flare style. Pick a color that complements your hat and that seems fitting for spring. Black just won't do, since it's too dark and drab.

It's also a good idea to skip wearing white, too. Things can get a bit muddy at Churchill Downs, and you just don't want to risk staining your dress.

Instead, think pastels and other colors that sing "spring." Sunny yellow, beautiful blue and verdant green are all good picks.

The weather can be a bit hit or miss on Derby Day, so it helps to plan your dress with care. A sleeveless or strappy sundress might be a good pick, if you luck out and the day dawns bright and the temperature climbs to 80 degrees. But, to be on the safe side, you might want to pick out a matching cardigan or jacket, so you have something to keep your arms warm in case the weather is anything less than nice.

If you need help deciding which dress best complements your hat and the rest of your outfit, it might be worth it to hire a stylist for the occasion to help you look pulled together and Derby chic.

3. The Shoes

One of the more common Derby Day fashion tips is the advice to bring not one, but two pairs of shoes to the event. Although the Derby itself is just two minutes long, the festivities begin early in the morning and stretch into the evening. That's a long time to stand in a pair of high heels.

For your own comfort, it's a good idea to pack a pair of stylish, comfy flats to wear during those long periods when you're standing around. A pair of flats will also make it a lot easier to walk on the cobblestones at Churchill Downs. If the ground is wet and muddy, you'll be glad to have a pair of flats to change into, instead of hobbling over the mud in a pair of heels.

You can skip the second pair of shoes if you're not attending Derby itself. Just make sure the pair you pick is comfortable enough for standing, walking and dancing in during your Derby day party. While heels are a traditional pick, if you're more comfortable in flats, don't be afraid to pick a pair that perfectly coordinates with your dress and hat.

4. The Purse

There are two Derby Day fashion rules to follow when it comes to your purse. Rule one is bring two bags. Rule two is make sure your bags don't exceed the size limits.


There's a limit of two bags per person at Derby. Neither bag can be bigger than 12 inches in any dimension. Use one bag to hold your essentials for the day, such as your flats, your sealed water bottle and your sunscreen. Use the other to hold your wallet, phone and other small necessities.

Think fashion when picking out your bag. Although a canvas tote will do well to hold your shoes and extras, it's not exactly going to match the rest of your outfit. Choose an elegant bag in colors that coordinate with your dress and hat.

5. The Jewelry

Just like your dress, you want to keep Derby Day jewelry pretty low key, so it doesn't clash with or detract from your hat. A simple strand of pearls, if you have them, is always a safe pick. If you'd rather adorn your wrists, choose a collection of thin, gold bangles or one larger cuff.

Derby Day: Men's Fashion

On Derby Day, men's fashion is just as important as women's fashion. The Derby is perhaps the one sporting event where wearing jeans and a jersey just isn't going to cut it for men. If you're a guy looking for advice on what to wear to Churchill Downs or to a Derby Day party, we've got you covered from top to toe:

1. The Hat

Although guys' hats at Derby aren't always as out-there as the ladies' hats, they are starting to get more and more flamboyant. If wearing a version of the racetrack in miniature on your head isn't your thing, you can always stick with a traditional fedora or a bowler hat. Go for a solid color, and you really can't go wrong.

If Derby Day dawns sunny, bright and warm, another option is to wear a straw hat. Whether it's a Panama hat or a boater, the straw will be lightweight enough to keep your head cool in the heat. Plus, the wider brim of the hat will keep the sun out of your eyes. Just make sure to skip the straw if it's going to rain, as nothing is more uncomfortable than trying to wear wet straw on top of your head.

2. The Tie

While women get to express themselves on Derby Day with their choice of hat, for men, it's usually all about the tie. Neck ties are normally the go-to, but some men do prefer their bow ties. Whether you go for a bow or a neck tie is really up to you.


Pick a tie in a fun and festive print to really liven up your outfit. You can find Derby-inspired ties covered in an embroidered mint julep pattern, for example. If you're going for pattern in another area of your outfit, such as your hat or vest, keep the tie simple. A solid color that coordinates with the rest of your look should work.

3. The Blazer, Vest and Shirt

The main pieces of your Derby Day outfit are the shirt, jacket or blazer, and vest. If you'll going to be in a suit, your jacket should match your pants. If you prefer a slightly more relaxed and casual Derby Day look, you can pair a blazer with coordinating — but not matching — pants.

Derby Day is the start of seersucker season, so if you want to be traditional, you can opt to wear a seersucker jacket and pants or a seersucker blazer.

If you're going to wear a vest, pick one in a light, springy color that coordinates with your jacket or suit. You are also free to skip the vest if you prefer. If you're going for a more casual — but still sharp — look, wear the vest without the jacket.

A crisp, clean, pressed white button-front shirt is always a good and safe bet for Derby Day. Don't be afraid to play with pattern and color, though, especially if you're played it safe with the rest of your look so far. Colorful gingham and stripes are always welcome at Derby.

4. The Pants

The ideal Derby Day pants are simple but colorful. Think of your favorite straight legged khakis, but done in a sun-drenched color. You will look right at home wearing a pair of cotton trousers in a bright green or vibrant melon shade. Sunny yellow and robin's egg blue are two more colors that are appropriate for Derby Day.

Just remember these two Derby Day fashion rules: Don't try and dress like a jockey, and make sure your pants coordinate with the rest of your look.

5. The Shoes

The leather horse-bit loafer, worn without socks, is a classic shoe choice for Derby. But you have a few other options, too. Two-tone wingtips are always stylish and appropriate for Derby. Another fail-safe pick is a pair of two-tone loafers.

Derby Day: Kids' Fashion


If you're bringing your little ones with you to the Kentucky Derby or to a Derby Day party, remember to dress them to impress, as well. Generally, that means following the same Derby Day fashion rules for men and women, but in miniature.

Little girls who love to play dress up will have a lot of fun picking out or even making their special Derby Day hat. Add a coordinating, simple dress and simple, flat shoes to complete the look.

Young gents can take a page from their father's or uncle's Derby style book and wear a colorful outfit that's perfect for spring. Few things look more dapper and cuter than a little guy in a seersucker suit, for example. Add a cute straw boater and a pair of loafers, and you'll have a little kid who's on the fast track to being a Derby Day heartbreaker.

For the youngest Derby fans, feel free to break from tradition and choose an outfit that is Derby-themed but not necessarily adult clothes in miniature. If your baby is still most comfortable in onesies, a horse-printed romper will not only look cute, but it will help make mid-Derby party diaper changes a snap. If your child is still in diapers, you're allowed to bring a diaper bag in with you to the event, so pick one that is festive and fun looking — horse print is optional.

Throwing A Derby Day Party?

Remember, it's not just Derby Day fashion that will make for a fun and memorable party. Hiring the right staff will help the day go without a hitch. If you need assistance recruiting a team to make your Derby Day party run smoothly, contact Quintessentially People today. We specialize in finding highly trained, qualified candidates for a variety of positions, from catering staff to personal stylists.