Kentucky Derby Hats: Fashion Must-Haves for the 2026 Run for the Roses

The 2026 Kentucky Derby is coming up on Saturday, May 2. The race is one of the most prestigious and best-loved horse races in the world. Run every year since 1875, it features 20 of the best three-year-olds going 1 ¼ miles for a $5 million purse and the honor of being remembered forever by horse racing fans.

Whether you’re going to Churchill Downs to experience the Kentucky Derby in person or you plan to watch and wager at your home Kentucky Derby party, wearing a fun Kentucky Derby hat is a tradition that makes the race all the more meaningful. Finding the right hat to go with your Kentucky Derby outfit is as much of a tradition as roses, mint juleps, and fast horses, so read on to find out how to become a part of this time-honored tradition.

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The Tradition of Kentucky Derby Hats

The Kentucky Derby began in 1875 as an American twist on the Epsom Derby, a grand tradition that dates back to 1780. Colonel Meriwether Lewis Clark, who built Churchill Downs, was deeply inspired by European racing traditions when establishing his new track in Louisville. That included the French system of pari-mutuel betting … as well as the English tradition of the Epsom Derby, a showcase for the top three-year-olds.

At the time, the Epsom Derby had a strict dress code for spectators who came to the race, including hats. So, that tradition of formality made it across the ocean – smart outfits and hats have been a Kentucky Derby tradition ever since Aristides won the first Kentucky Derby in 1875.

Though Churchill Downs does not mandate hats at the Kentucky Derby, they remain as popular as ever. And, it’s no surprise! Whether you’re enjoying the Kentucky Derby in the most exclusive boxes or in the chaotic and casual infield, the right hat will tie together your look and help keep the sun out of your face.

Proper Kentucky Derby Attire

With over 150,000 people attending the Kentucky Derby at Churchill Downs and millions more enjoying Derby day from their local racetrack, a neighborhood bar, or a house party, proper Kentucky Derby attire varies based on the experience you want to have.

Dress for the Weather

One thing to take into account, both with your hat and your clothing, is the weather and how much time you will spend outside. If you’re0 going to be in an air-conditioned box all day, or hanging out inside a house or a bar, weather and comfort might be less of a concern. But, if you’re going to be walking around either Churchill Downs or your local racetrack, make sure you’re wearing shoes that are practical enough to walk around in, or clothing that won’t cause you to overheat, since Kentucky Derby day can be hot!

Kentucky Derby Dress Code

If you’re sitting in one of the exclusive boxes at Churchill Downs or you are attending a Kentucky Derby party at a fancy place, dress for the occasion! This especially holds true if you are sitting in the parts of Churchill Downs that have dress codes. Some parts of the track only prohibit things like torn clothes, crop tops, and flip-flops, while other parts require jackets, collared shirts, dresses, or pantsuits. Make sure to check the racetrack website before you go, to make sure you know the restrictions for where your tickets are located.

If you’re in the most casual locations, like the infield party at the Kentucky Derby, a chill watch party on your friend’s couch, or a local sports bar, you can dress a lot more casually. There may not be a dress code where you plan to celebrate Kentucky Derby day.

No matter where you’re planning on watching the race, a Kentucky Derby hat is always appropriate. After all, it’s tradition. If the idea of wearing a fashionable Kentucky Derby hat sounds like something you’ve always wanted to try, it’s a great idea, and there’s no year like this year to get to know your Kentucky Derby hat options and pick the perfect one!

Choosing the Perfect Hat

The most fun thing about fashion is that the thing that matters the most is your own personal taste. So, first and foremost, wear what makes you happy.

If trying the newest trend excites you the most, that’s a perfect reason to choose a Kentucky Derby hat. If a horse you love in the race wears silks that are pink, or red, or blue, or green, or black? Wear a hat to match those silks! If you’re going to the Kentucky Derby with a group of close friends and want to coordinate hat colors, shapes, or patterns? That’s always a hit!

Understanding types of Kentucky Derby hats

If you’re looking for the perfect Kentucky Derby hat but you’ve never been much of a hat person, it’s never too late to start! These are some of the most popular kinds of hats that you’ll find when you’re shopping for Kentucky Derby hats, and that you’ll see at the racetrack and at parties! Let these tips give you inspiration for choosing your look.

• Boater hats: Boater hats are a classic, light, warm-weather hat. Often made of straw, with a classic flat crown and stiff brim, they are most popular for masculine styles, but there are also modern, feminine boater-inspired hats made of a wide range of materials. The classic boater is wrapped with a solid or striped ribbon, a fun touch to coordinate with the rest of an outfit.
• Bowler hats: A rigid, rounded felt hat, a bowler hat has a short, curved brim, making it less practical for sun protection. However, they’re the perfect finish to an old-school gentlemanly look. Bowler hats are also a part of Kentucky Derby history – in the United States, they’re also called Derby hats because so many people would wear them to horse races like the Epsom Derby in late 1800s England!
• Cartwheel hats: As the name suggests, a cartwheel hat is an extremely wide-brimmed hat. These hats came into fashion back in the 1910s and have been a staple ever since. Famous actresses and even royalty over the decades have worn cartwheel hats, and they are a striking addition to any Kentucky Derby outfit. And, the wide brim provides practical shade from the sun, so they’re a great choice for outdoor settings.
• Fascinators: Strictly speaking, a fascinator is not a hat, but rather a decoration attached to the head with a comb, clip, or headband. Fascinators are very popular at the Kentucky Derby and at other fashionable race meets like Royal Ascot. They can be made of feathers, flowers, lace, ribbon, or other creative materials. They aren’t practical for providing shade from the sun, but they are cute, creative, and a classic Kentucky Derby choice.
• Fedoras: With an indented crown and prominent but not oversized brim, fedoras have been popular since Sarah Bernhardt played the title role in the Victorien Sardou play Fédora in the late 19th century. Especially if you go the seersucker or pastel route, a straw fedora with a complementary-colored hat band never goes out of style for Kentucky Derby day.
• Pillbox hats: If simple elegance is your style, the pillbox is your hat. A straight-sided, brimless hat style, a pillbox hat in a color that either matches or complements a dress or jacket, is a timeless addition to a Kentucky Derby outfit. And, if you want a slightly less simple take on the pillbox hat, consider topping it with a flower or feather decoration, or adding a veil.

Of course, these are only a few of the most popular choices for Kentucky Derby hats. On the first Saturday in May, you can wear any kind of hat that fits your personality!

Hat Trends: Derby Hats, Fascinators, and More for 2026

Don’t be afraid to wear something elegant and timeless to the Run for the Roses: it’s a historic event, so that is always going to be appropriate. But, if you want to stand on the cutting edge of fashion, here are some fabulous trends to consider for 2026:

• Bold florals: At the 2026 hat show at the Kentucky Derby museum, flowers in vibrant colors were the order of the day. They were particularly common in warm and hot colors: think red, orange, yellow, pink. Whether you’re going literal – flowers that look just like the roses on the blanket given to the winner – or more suggestive, like orange and yellow leaves that suggest a sunburst? Blazing, bold florals will pop at the Derby in 2026.
• Bows, beautiful bows: Town and Country Magazine’s recommendations for 2026 Kentucky Derby hats feature bows, bows, and more bows. From one structured bow over the front of the face on a traditional floppy hat, to entire fascinators shaped like one large bow, to an entire hat looking like a flock of butterflies, each of whose wings suggests one vividly colored bow? Your style will stand out if you go with bows.
• Fancy little hats: After the spring-summer 2026 fashion shows, Harper’s Bazaar called 2026 the year of the “fancy little hat.” From pillboxes to newsboys to crocheted, art deco skullcaps, the runways during fashion week were full of small, structured, and deeply classic hats. Everything old is new again, so feel free to bring back your grandparents’ favorite piece, or find a new hat that riffs on those classic styles.

Shopping for Your Kentucky Derby Hat

Now you know all about Kentucky Derby hats, and all that’s left to do is to find the hat or fascinator of your dreams!

No matter where you live, you always have the option of shopping online for a Kentucky Derby hat you’ll love. The best thing about shopping online is that you have an entire world of choices: every kind of hat under the sun is sold online! Just make sure that the hat is within your budget, and that the seller can ship your hat to you in time for the first Saturday in May. It’s also a good idea to check reviews if you have never purchased hats or other fashion items from the retailer before, just to make sure that what you see online is what you are being sold.

You may prefer to find your dream Kentucky Derby hat in person. It may take more time to go out and browse brick-and-mortar stores, and depending on whether you live in a small town or a large city, you may not have as many choices.

On the other hand, there is a great personal touch when shopping in person. You can get together with your friends and try the hats on with each other. You’ll know what they look like on you, and you can get feedback from your friends about how it looks. You might even want to do your hat shopping during a day at the track—some racetracks have on-site milliners who can help you pick out a fashionable hat.

When shopping in person, you can also take the hat home with you that day, meaning you don’t have to stress out about whether your dream hat will be delivered to your house before Kentucky Derby day.

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