The Kentucky Derby is renowned not only for its horse racing but also for the extravagant hats worn by attendees, a tradition with roots in British and French fashion observed by the Derby's founder, Colonel Meriwether Lewis Clark Jr., during his travels. The event, held at Churchill Downs, showcases a dazzling array of outfits, with hats being the most eye-catching element, believed to bring good luck the larger they are. Milliners like Jenny Pfanenstiel cater to the demand for unique, standout designs, as attendees seek to express their personality through their headwear. Despite the lack of formal dress code for hats, it is an unwritten norm to wear something on one's head to avoid standing out for the wrong reasons. Celebrated for its pageantry, the Kentucky Derby's fashion tradition has naturally evolved, reinforcing its status as a significant cultural and social affair.

The Kentucky Derby, hosted at Churchill Downs, is a premier horse racing event where fashion, particularly hats, plays a central role, with attendees dressing in elaborate outfits including large, opulent headwear.

The tradition of wearing extravagant hats at the Derby originates from Colonel Meriwether Lewis Clark Jr.'s observations of British and French racing fashion, where spectators donned elegant headwear, influencing the Derby's own fashion norms.

Attendees believe that larger hats bring more luck, a notion that has fueled the tradition of wearing oversized and decorative hats, especially among women, to the event.

Milliners such as Jenny Pfanenstiel are in high demand during the Derby season, creating custom, one-of-a-kind hats that reflect the wearer's personality, ensuring their uniqueness in the crowd.

Although there is no official requirement for wearing hats at the Derby, it is an unwritten rule that one should do so to blend in, as not wearing a hat would make one conspicuously out of place.

The Kentucky Derby's fashion, particularly the hat tradition, has naturally evolved over time, becoming an integral part of the event's cultural and social appeal, drawing both celebrities and fashion enthusiasts.

Bryan Murphy, a content producer for The Sporting News, provides coverage of this iconic event, highlighting its significance and the ongoing fascination with its fashion elements.

Break out your best fedora or fascinator. It's time for the Kentucky Derby. 

The premiere horse racing event of the season is this weekend, as 20 horses and their jockeys will gallop for the 1.25 miles with the hope that they cross the finish line first. 

The scene at Churchill Downs is always an extravagant one. While there are plenty of high-profile celebrities that attend the event, everyone in attendance is dressed to the nines. From fancy dresses to pristine suits, the outfits at the Kentucky Derby are sights to behold. 

While the tops and bottoms are always intriguing, there is nothing that compares to the hats that are worn at the race track. The bigger, the better when it comes to the lids people sport at the Kentucky Derby. 

What is the history behind the hats at the Kentucky Derby? The Sporting News explains. 

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Kentucky Derby hats tradition, explained

The history of the extravagant derby hats dates all the way to the early days of the event, and has British and French ties, according to Jessica Whitehead, curator of collections at the Kentucky Derby Museum in Louisville. 

Colonel Meriwether Lewis Clark Jr. — the man who helped establish the Kentucky Derby and founded Churchill Downs — went to England and France in the time before the inaugural Kentucky Derby happened in 1975. While in the countries, he and his wife, Mary, took notice of the apparel at the races, noting that all of the viewers were wearing elegant outfits. 

"[They] were impressed with the pageantry and opulence of the spectators' fashions, including headwear," Whitehead said. "... Since that time, the [Derby’s] fashion tradition has developed quite naturally."

The hats were a part of those fashion statements. While a majority of sporting events don't require any specific outfit to be worn, that's not necessarily the case at the Kentucky Derby.

"Generally, people don’t think about what they’re wearing to sporting events, but [with] racing you do, and it’s obviously something that’s really important because it’s kept on going," Christine Moore said, who is a New-York based milliner. 

But why the size of the hats? It's not just a small little cap that is worn by the women and men in attendance. The hats, especially on the female side, are large and over-the-top, but there is a reason behind it. 

"So people thought the bigger the hat, the bigger the luck," Jenny Pfanenstiel said, a milliner from Louisville. "So that's where the big brims came into play, and it just stuck."

There are no specific requirements put in place at the race track in terms of headwear. However, it's an unwritten rule to wear something on your head — otherwise, you will be sticking out like a sore thumb. 

"If you're wearing something on your head, that's all that matters," Pfanenstiel said. "Because if you're not, you'll be the one sticking out."