21 Creative Kentucky Derby Hat Contest Ideas

If you want some amazing Kentucky Derby hat contest ideas, my 21 top picks will help you. From classic to modern, these ideas will inspire you to create a winning hat that will make heads turn at any derby event.

kentucky derby hat contest ideas

What Is the Kentucky Derby Hat Contest?

The Kentucky Derby Hat Contest is an annual event held during the Kentucky Derby, a prestigious horse racing event in Louisville, Kentucky. This tradition dates back to the early days of the Derby and has become an integral part of the overall experience for attendees.

At the hat contest, participants showcase their creativity by wearing extravagant hats that range from elegant and sophisticated to over-the-top and outrageous. The hats are judged based on their originality, style, and overall presentation.

Why Participate In a Kentucky Derby Hat Contest?

Participating in a Kentucky Derby Hat Contest is not only a fun and exciting experience but also a great opportunity to express your creativity and fashion sense. It’s a chance to stand out from the crowd and make a statement with your unique and eye-catching hat.

Moreover, the contest often offers cash prizes for the winners, making it a worthwhile competition to enter. And let’s not forget the bragging rights of winning a derby hat contest!

21 Creative Kentucky Derby Hat Contest Ideas

How do you decorate a Kentucky Derby hat? Here are the details of my 21 top Kentucky Derby hat contest ideas. 

#1. Roses and Ribbons Extravaganza

Picture this: a hat brimming with the lush red of roses, interwoven with ribbons that dance in the breeze. Attendees can draw inspiration from the Derby’s iconic flower, crafting headpieces that symbolize the Run for the Roses. It’s not just a hat; it’s a wearable rose garden topped with ribbons that add a touch of elegance.

#2. Equestrian Elegance

Channel the spirit of thoroughbred legends with hats adorned with miniature horses, horseshoes, and bits. This theme pays homage to the heart of the event—the majestic horses. Imagine a sea of spectators, their hats a nod to the equine stars, turning the stands into a carousel of equestrian tribute.

#3. Old Kentucky Glamour

Encourage participants to embody the Golden Age of the Derby with hats featuring vintage styles, feathers, and pearls. Think of the grandeur of The Great Gatsby meeting the Kentucky Derby—a blend that’ll have heads turning faster than the horses on the track.

#4. Bourbon Street Boater

Take a swig of inspiration from Kentucky’s bourbon heritage. Deck out boater hats with bourbon bottle replicas, oak barrel accents, and amber-colored adornments. This idea celebrates Kentucky’s famed spirit, ensuring that each hat is as smooth and fiery as the drink itself.

#5. Derby Day Garden Party

Invite nature lovers to bring a garden party to their hats, complete with artificial butterflies, birds, and blooms. This idea transforms the spectator stands into a fluttering, blossoming parade that mirrors the springtime glory of Derby Day.

#6. Bluegrass Bonanza

Nothing screams Kentucky like the bluegrass for which it’s famous. Contestants can pepper their hats with bluegrass blades, musical notes, and perhaps even a banjo or two. It’s a tip of the hat to the state’s musical roots, creating a symphony in hat form.

#7. Mint Julep Madness

Celebrate the Derby’s signature cocktail with hats that boast mint sprigs, ice-cube shapes, and julep cup designs. This idea is a fresh breath of fun, stirring up a concoction of creativity as attendees parade their minty-fresh masterpieces.

#8. Southern Belle Soirée

Encourage a dash of Southern charm with wide-brimmed hats, delicate lace, and a sprinkle of southern belle attitude. This theme is a heartfelt tribute to Southern hospitality, inviting a genteel elegance to the Derby hat parade.

#9. Racing Silks Spectacle

Take cues from the jockeys’ vibrant silks. Contestants can mirror the patterns and colors of their favorite jockey’s outfit in their hat designs, turning the crowd into a rainbow reminiscent of the racetrack itself.

#10. Paddock to the Podium

Let’s not forget the paddock! Designs can incorporate elements from the paddock area—greenery, picket fence motifs, and even a tiny winner’s circle. This concept brings the behind-the-scenes action right to the forefront.

#11. Whimsical Weather Vane

With the weather vane an iconic symbol of the Derby, why not fashion hats that reach for the sky? Participants could craft towering creations with a nod to this tradition, perhaps even including a movable arrow to really catch the eye.

#12. Lucky Horseshoe Haven

Luck plays a big part in the Derby. Encourage hat makers to sprinkle a bit of that lucky magic into their creations, with horseshoes turned upward to catch good fortune. These hats might just become personal talismans for the day!

#13. Derby Dapper Dan

Let’s hear it for the gents! A category for the most dapper men’s hat, complete with bow ties, pocket squares, and the polished look of a true Southern gentleman. It’s a chance for the fellas to strut their stuff with panache.

#14. Winner’s Circle Wreath

Why not let participants wear their own winner’s wreath? Hats adorned with the same greenery and flowers that drape over the victorious horse give everyone a taste of triumph.

#15. At the Starting Gate

Inspire designs that feature elements of the starting gate—metallic bars, horse figures poised for action, and even sound effects. It’s the thrill of the race’s beginning, captured on a hat!

#16. Sunset Over the Stables

As the day wanes, the skies over Kentucky light up. Hats that reflect the stunning sunsets, with hues of pink, orange, and purple, bring the beauty of the evening sky to the competition.

#17. Derby Decadence

Encourage over-the-top luxury with hats that drip with faux jewels, feathers, and a touch of golden glam. It’s the luxury of the Derby, concentrated into extravagant headwear.

#18. Infield Festivity

The infield is where the party’s at. Think festival-themed hats, complete with mocktail umbrellas, party favors, and a spirit of jubilant chaos. It’s the fun of the infield; no mud is required!

#19. Tip of the Hat to Tradition

A category that honors the long history of the Derby with traditional elements—black-eyed Susans, antique brooches, and images from Derby’s past. This idea wraps the rich tapestry of the event’s heritage into every stitch and feather.

#20. Star-Spangled Derby

A patriotic twist with hats that showcase stars and stripes, eagles, and the red, white, and blue. It salutes American tradition, with the Derby as the backdrop.

#21. My Old Kentucky Home

Lastly, a heartfelt homage to the state song. Designs could feature Kentucky state symbols, musical notes, and celebrating the Commonwealth’s beauty. It’s about pride, place, and the pure heart of Kentucky.

Read also: 21 Easy & Creative Bookmark contest ideas

How to Host the Kentucky Derby Hat Contest?

The Kentucky Derby is one of the most popular horse racing events in the world, and the hat contest has become a tradition that garners much attention. Hosting a successful Kentucky Derby hat contest can be a fun and exciting way to celebrate the event. Here are twelve steps to help you host an unforgettable Kentucky Derby hat contest.

Step 1: Select a Venue

The first step in hosting a Kentucky Derby hat contest is to select a suitable venue. The venue should be spacious enough to accommodate the contestants and spectators, and it should be visually appealing to enhance the overall experience of the event.

Step 2: Determine the Rules and Regulations

To ensure that the hat contest runs smoothly, it is essential to establish clear rules and regulations. This includes criteria for judging the hats, eligibility requirements, and submission timelines.

Step 3: Set the Theme

A Kentucky Derby Hat Contest is incomplete without a theme. Determine what theme you want for your hat contest and communicate that early to encourage contestants to follow the theme.

Step 4: Advertise

This is an important step in hosting a successful Kentucky Derby hat contest – advertising. Use multiple platforms to inform people about the contest and what they can expect. Utilizing social media platforms, local TV, and radio stations can increase the event’s visibility.

Step 5: Recruit Judges

Your judges should be people with experience and knowledge of fashion and trends. You could also have experts on hats and headwear to participate as judges.

Step 6: Set up a Registration System

Registration must be simple and must be fully accessible online. Keep track of registrations and make sure that all entrants meet eligibility requirements.

Step 7: Establish a Timeline

A prearranged timetable is essential so that there is no confusion among contestants and the event runs smoothly. Make sure that all the deadlines and critical dates are communicated in advance of the event.

Step 8: Prepare the Venue

Before the event begins, it would be essential to have the venue arranged. Be sure to arrange for chairs, tables, and any other equipment you need. Remember to create a special section for contestants’ photo opportunities.

Step 9: Organize the Contestant’s Line Up

Prepare a line-up system to ensure that contestants take part in the contest in the correct order. This will help to create a better flow of the event.

Step 10: Broadcast the Event

Using social media and other broadcasting channels, you can ensure the event reaches a wider audience. Livestreaming on various platforms like Facebook and Instagram can introduce the event to an unlimited audience.

Step 11: Prepare the Awards

To encourage more participation in future Kentucky Derby hat contests, have well-structured award categories. For example, the “Best Traditional Hat,” “Most Creative Hat,” and “Best Overall Hat” categories can be awarded.

Step 12: Announce the Winners 

The final and most exciting step is to declare the winners of the Kentucky Derby hat contest. Use presentations to announce the winners and keep a little suspense for the final winner. Make sure to let the contestants and spectators know when and where they can get their pictures taken and possibly enjoy the awards ceremony.

Check out the below video on making a DIY Kentucky Derby hat

12 Prize Ideas for the Kentucky Hat Contest 

Here, I have got 12 amazing prize ideas for the Kentucky Hat contest.

#1. Grand Prize: A VIP Tour of Churchill Downs Racetrack

The grand prize for the Kentucky Hat Contest could be a VIP tour of the famous Churchill Downs Racetrack. The Churchill Downs is often referred to as the home of the Kentucky Derby, which is the oldest continuously held horse race in the United States. 

The tour could include a visit to the stables, the museum, and the infield. The winner would also get an opportunity to meet some of the famous trainers and jockeys who have graced the tracks of Churchill Downs. This prize would be an unforgettable experience for any horse racing enthusiast. 

#2. Exclusive Dinner at a Celebrity Chef’s Restaurant

The second prize could be a dinner for two at a celebrity chef’s restaurant in Kentucky. Kentucky is home to some of the best chefs in the country, and this prize would give the winner a chance to taste some of the finest cuisine in the state. The winner could enjoy a unique dining experience at a top-rated restaurant, and the prize could include transportation to and from the restaurant. This prize would make the winner feel like a celebrity for the night.

#3. A Hot-Air Balloon Ride over Kentucky’s Countryside

A hot-air balloon ride over the picturesque countryside of Kentucky would be an excellent prize for nature lovers. Kentucky has beautiful rolling hills and scenic views, which would be a treat for anyone who loves to explore the great outdoors. 

The winner could take a hot-air balloon ride and enjoy panoramic views of the countryside. This prize would be an unforgettable experience for anyone who loves adventure and nature.

#4. An Afternoon Picnic at a Local Vineyard

Kentucky has many vineyards and wineries where visitors can sample the state’s finest wines. A relaxed afternoon picnic at a local vineyard could be an excellent prize for those who appreciate good wine and enjoy outdoor spending. 

The picnic could include a selection of local cheeses, fruits, and snacks. The winner could relax in the beautiful surroundings of the vineyard and soak in the beauty of the location.

#5. A Unique Bourbon Tasting Experience

Kentucky is famous for its bourbon, and a unique bourbon-tasting experience could be an excellent prize for bourbon lovers. The winner could get a chance to visit a local distillery and sample various bourbons. 

The distillery tour could also include a detailed explanation of the distilling process and the history of bourbon in the state. This prize would be a dream come true for anyone who loves bourbon.

#6. A Weekend Stay at a Luxury Mountain Resort

Kentucky has many luxury mountain resorts, and a weekend stay at one of these resorts could be an excellent prize for someone who needs a break from the hustle and bustle of everyday life. 

The winner could enjoy a relaxing spa treatment, activities such as hiking, fishing, or horseback riding, and meals at the resort’s restaurant. This prize would be a perfect way to unwind and destress.

#7. A Private Tour of the Maker’s Mark Distillery

The Maker’s Mark Distillery is one of the most famous distilleries in Kentucky, and a private tour of the facility could be an impressive prize. The winner could learn about the history of Maker’s Mark and the process of making the famous Kentucky bourbon. 

The tour could include a visit to the aging warehouse and the bottling line. This prize would be a memorable experience for any bourbon enthusiast.

#8. A Day on Kentucky Lake

Kentucky Lake is one of the largest man-made lakes in the United States and offers many activities, such as fishing, boating, and kayaking. A day on Kentucky Lake could be a fantastic prize for someone who loves water sports. 

The winner could rent a boat and explore the lake or spend the day fishing. This prize would be a unique way to enjoy the natural beauty of Kentucky.

#9. A Visit to Mammoth Cave National Park

Mammoth Cave National Park is one of the most visited national parks in the United States. The park is home to the world’s longest-known cave system, and a visit to the park could be an excellent prize for someone who loves nature and adventure.

The winner could take a guided cave tour or explore the park’s many hiking trails. This prize would be a once-in-a-lifetime experience.

#10. A Helicopter Tour of Kentucky’s Famous Horse Farms

Kentucky is synonymous with horse racing, and a helicopter tour of some of the state’s most famous horse farms would be a thrilling prize for any racing fan. The winner could take a bird’s eye view of the horse farms that have produced some of the world’s greatest racehorses. 

They could also get an opportunity to see the horses in training or relax in the paddocks. This prize would be a unique way to experience Kentucky’s racing heritage.

#11. A Private Tour of Kentucky’s Best Bourbon Bars

Kentucky has some of the best bourbon bars in the United States, and a private tour of these bars could be a fantastic prize for bourbon enthusiasts. The winner could visit some of the most exclusive and famous bourbon bars in the state and sample unique bourbons that are not available anywhere else. This prize would be a dream come true for any bourbon lover.

#12. Tickets to a Kentucky Basketball Game

Last but certainly not least, tickets to a University of Kentucky basketball game could be the ultimate prize for any sports fan. The University of Kentucky is known for its powerhouse basketball team, and a chance to watch them play in person would be a dream come true for many. 

The winner could experience the electrifying atmosphere of a college basketball game and witness some of the best players in the country in action. This prize would be an unforgettable experience for any sports lover.  

FAQs on Kentucky Derby Hat Contest Ideas

Who wears hats to the Kentucky Derby?

Hats have been a longstanding tradition at the Kentucky Derby, especially for women. The Kentucky Derby is one of the most fashionable events of the year, drawing in crowds not only for the horse racing but also for the spectacular hats worn by attendees.

Women attending the Kentucky Derby traditionally adorn themselves with extravagant and over-the-top hats. These eye-catching hats often serve as a statement piece and make a fashion statement. Women who wear hats to the Kentucky Derby often choose ones with bold colors and intricate designs, with many opting for wide brims, feathers, and flowers.

Wearing a hat to the Kentucky Derby is not only a fashion statement but also a way to pay homage to the event’s rich history. Each year, the Kentucky Derby Hat Parade takes place, showcasing the most captivating hats worn by attendees. In addition, the race track’s infield, known as the “People’s Party,” is filled with women wearing hats of all styles and colors.

When did Derby hats start?

“What is a derby hat called?” Derby hats, also known as bowler hats, have become an iconic fashion accessory over the years. These hats have a unique design that sets them apart from other types of headwear, and they have a rich history that dates back to the 19th century. The origins of the Derby hat can be traced back to the year 1849 when Edward Coke first commissioned a hat to be made for his gamekeepers.

The commission was given to Thomas Bowler, a renowned hat maker. He was tasked with creating a hat that would be more practical for the gamekeepers to wear while on the job. This led to the creation of the Derby hat, which was designed to withstand the often harsh outdoor conditions faced by gamekeepers.

The Derby hat features a round crown and a short brim, which provides excellent protection from the sun. It was also designed to be sturdy, with a hard-felt construction that could withstand the elements. This made the Derby hat a popular choice not only for gamekeepers but also for other outdoor workers such as farmers, railroad workers, and laborers.

Over time, the Derby hat became popular among the general population, and it was worn as a trendy fashion accessory. This led to various modifications being made to the hat’s design to make it more fashionable. For instance, the crown’s shape was altered, and the brim was made narrower.

In the early 20th century, the Derby hat reached its peak of popularity, with it being worn by prominent figures such as Charlie Chaplin and Winston Churchill. However, by the mid-20th century, its popularity began to wane, and it became less common to see people wearing it.

What is the story behind the Kentucky Derby hats?

The Kentucky Derby is a prestigious horse racing event that has been an important part of the American social calendar since its inception in 1875. One of the most iconic aspects of the Kentucky Derby is the tradition of wearing extravagant hats, which has become an integral part of the event. The story behind the Kentucky Derby hats is rooted in the event’s origin and its founder, Colonel Meriwether Lewis Clark Jr.

Colonel Meriwether Lewis Clark Jr. founded the Kentucky Derby in 1875 after being inspired by the European horse racing scene. In particular, he was impressed by the high-class racing events in England and France, where attendees would dress in their finest attire, including elaborate hats. 

To recreate that European ambiance, Colonel Clark Jr. encouraged attendees to dress up and sport their finest headwear, hence beginning the tradition of wearing hats to the Kentucky Derby.

As the event grew more popular, so too did the elaborate hats worn by attendees. In the 1920s, women began wearing more extravagant and flamboyant hats as a way to stand out and attract attention. Over the years, the hats have evolved into an essential part of the Kentucky Derby, and many people consider them just as important as the horses themselves.

Today, the Kentucky Derby hats have become a symbol of American fashion and culture and have been worn by some of the most famous people in the world. Each year, millions of viewers watch the event on television or attend in person, hoping to catch a glimpse of the most extravagant and eye-catching hats.


Hopefully, you have a detailed idea of all the Kentucky hat contest ideas. Each idea is unique and offers a different experience for the winner. Whether you are a foodie, nature lover, or sports fan, there is something in Kentucky for everyone. 

So why not plan a trip to this beautiful state and try out some of these activities yourself? Who knows, you might even be lucky enough to win one of these amazing prizes! So start planning your next adventure in the Bluegrass State and experience all that Kentucky has to offer. The possibilities are endless!

Julia Nancy
Julia Nancy

I have vast experience arranging online voting contests for hundreds of clients worldwide in the last 8 years. I also helped countless clients to win their online competitions. Here, on royalvotes.com, I am just sharing knowledge from my experiences. If you need any help regarding the online contest, email me at julia@royalvotes.com