Kentucky Derby hats, explained: Why horse racing fans wear extravagant headwear at the event | Sporting News Canada

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. 

BUY NOW: Kentucky Derby hats for men | Kentucky Derby hats for women

Kentucky Derby hats, 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.”

MORE: Who will win the Kentucky Derby? Horses, odds, expert picks 

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.”

MORE: Breaking down the full draw for the 2024 Kentucky Derby

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.”