The history behind those extravagant Kentucky Derby hats

Why the right Kentucky Derby hat is crucial for the big event

This Saturday, May 4, is an exciting day. It’s the 2024 Kentucky Derby — specifically, the 150th running of the horse race held at Churchill Downs on the first Saturday of every May.

And if there is anything that can overshadow the race, it is the fashion. If you’ve ever wondered about the backstory behind those gloriously extravagant headpieces, you’ve come to the right place. While these famed hats were originally worn by women, today, men also enjoy wearing their own styles to the event. We rounded up the best Kentucky Derby hats for women and men to sport this spring.

In this article: Forbusite Church Kentucky Dress Derby HatWomen’s Organza Church Kentucky Derby Hat and Belfry Pure Wool Bowler Derby Hat

A brief history of the Kentucky Derby hat

Col. Meriwether Lewis Clark Jr. was the founder of the Louisville Jockey Club and the builder of Churchill Downs, where the Kentucky Derby is held. His vision for the race was always to have it be a high-class event that attracted the elite members of society.

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To catch his targeted audience’s attention, Clark used high-class women to create a draw. Consequently, attending a horse race was a chance to show your style. These events quickly became as much known for dazzling fashions as they were for the actual race.

However, this was back in 1875. Over the next 100 years, the rules of fashion loosened a bit. In 1952, CBS broadcast the Kentucky Derby for the first time. This meant attendees didn’t just have to stand out in a crowd, they wanted to be seen on national television. The result? Derby fashion became even bigger, more extravagant, and brighter.

Because a hat could be seen in even the biggest crowd, these magnificent accessories became the focal point. The tradition has remained. If you want to make an impression at the Kentucky Derby, the right hat is the way to do it.

Best Kentucky Derby hats

Women’s Kentucky Derby hats

Forbusite Church Kentucky Dress Derby Hat

Forbusite Church Kentucky Dress Derby Hat
This sophisticated hat covers the head and swoops down over the eye to add a chic element of style. You could wear it to any formal occasion where you want to impress, including the Kentucky Derby. It’s available in more subtle neutral shades as well as a few brighter ones. Certain styles even have jewel embellishments for a more attention-grabbing look.

Cizoe Fascinators Kentucky Derby Headband

Cizoe Fascinators Kentucky Derby Headband
For a more dynamic flash of subtle elegance, consider this headband in burgundy, a bold and trendy color for spring 2024. It is easy to put on and can be positioned in a variety of ways, letting you create your own fashion statement. If you’re not set on burgundy, it comes in 27 other colors.

Best Women's Organza Church Kentucky Derby Hat

Women’s Organza Church Kentucky Derby Hat
This sheer black hat slays. It would be perfect for Wednesday Addams or anyone else who wants to turn heads with a bold fashion statement. It is elegant, stylish and unforgettable. You can get this hat in 19 other styles, too. 

F&N Story Ladies Kentucky Derby Hat

F&N Story Ladies Kentucky Derby Hat
This striking pink hat is perfect for rocking Barbiecore, which is still going strong in 2024. When you wear it, you will be trendy and chic, and it will definitely pop in a crowd. The pop of color and floral beauty can help ensure you are the center of attention. There are seven other styles to choose from, as well. 

Best Fascinators Kentucky Derby Flapper Headpiece

Fascinators Kentucky Derby Flapper Headpiece
For a little throwback style, consider this headpiece. It has a veil, feathers and a bold flower reminiscent of the flapper subculture of the Roaring ’20s. The chic nostalgia makes it perfect for your Kentucky Derby-themed event. There are a staggering 49 styles to consider for this accessory. 

Men’s Kentucky Derby hats

Belfry Pure Wool Bowler Derby Hat

Belfry Pure Wool Bowler Derby Hat

The original Kentucky Derby hat for men was the bowler hat. This one has a feather detail for extra flair. Since it’s made of wool, it’s not the best choice for warm weather, but it will look the most authentic. It comes in five neutral colors.

Pineapple&Star Unisex Straw Fedora Hat

Pineapple&Star Unisex Straw Fedora Hat

When it comes to hats for the Kentucky Derby, a man can’t go wrong with a classic fedora. This lightweight and breathable hat offers SPF 50+ sun protection, so it’s also great for the beach or as resort wear. You can get it in 18 styles.

LADYBRO Men's Trilby Hat

LADYBRO Men’s Trilby Hat

A trilby hat is similar to a fedora but with a shorter brim angled down for a jauntier look. It’s a solid Kentucky Derby hat for men, available in straw and wool versions. If you want to stay cool, go with the straw version. Between the two versions, there are 27 colors to choose from.

Voboom Men's Newsboy Hat

Voboom Men’s Newsboy Hat

If you want to look dapper and sporty, go with a newsboy cap. It’s made of breathable cotton, so you won’t get too hot in the sun. This cap comes in 10 colors. It’s also a stylish accessory for golfing — even hunting if you go with the camouflage pattern. 

Zakira Straw Boater Hat

Zakira Straw Boater Hat

For those who really want to go old school, a boater hat is just right. This straw boater will keep you cool while helping you stand out from the crowd. It comes in five styles with different ribbon colors along the brim. 

Prices listed reflect time and date of publication and are subject to change.

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