Stylish Kentucky Derby Hats: Your Guide to This Year’s Must-Haves

The Kentucky Derby has happened at Churchill Downs in Louisville, Kentucky, every year since 1875. The Run for the Roses is one of the most prestigious horse races in the world: up to 20 top three-year-olds run 1 ¼ miles for a $5 million purse and a share of horse racing history.

Part of the fun of horse racing, though, is that you don’t have to own a horse in the race to have a great time. Whether you’re going to Louisville or throwing a Kentucky Derby party at home, you can place your bets on your favorite horse, and you can dress up for the occasion. Fashion, including Kentucky Derby hats, is just as much of a part of Kentucky Derby history as fast horses, the blanket of roses, and delicious mint juleps.

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Why Kentucky Derby Hats Are a Tradition

Kentucky Derby hats go back to Colonel Meriwether Lewis, Jr.’s idea to model classic races at Churchill Downs, including the Kentucky Derby, off the most important races of the British racing year. In the 19th century, the Epsom Derby had already been a tradition for almost a century, and in those days, there was a strict dress code for all race attendees, including hats. So, people have been wearing hats to the Kentucky Derby ever since its first running in 1875.

Even though the dress code at Churchill Downs does not mandate hats at the Kentucky Derby, hats have remained popular through the century and a half of the race’s history. That’s no surprise. Hats are not only a fun fashion accessory for formal, semi-formal, and even casual occasions, but they’re also a great way to keep the sun off your head (and even shoulders, if your hat is floppy enough!) during a day at the racetrack.

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’re 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? 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 a great idea!

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!

• 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.
• Cartwheel hats: As the name suggests, a cartwheel hat is a hat with a very wide brim. 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 options for Kentucky Derby hats. On the first Saturday in May, you can wear any kind of hat that makes you feel good!

Finding Your Dream Derby Hats

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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