The Kentucky Derby A Celebration Not Only of Horses, but also of Hats!

“In your Easter bonnet With all the frills upon it You’ll be the grandest lady in the Easter parade

I’ll be all in clover And when they look you over I’ll be the proudest fellow in the Easter parade”

Irving Berlin 1933

Hats and horses go together from Ascot to the Melbourne Cup even at Pattaya’s own Pink Polo Day! From fascinators to small and big creations, hats are a must and in Louisville,”Derby style” is celebrated big-time. Highly anticipated, the Kentucky Derby is the oldest running thoroughbred horse race in the world, held on the first Saturday of the month of May, and the ladies of Louisville, KY, are already out choosing their hats.The Derby is the longest continually held sporting event in the United States, and attending the Kentucky Derby is a big deal. You need to look good. It’s quite the fashion event.

Often referred to as “The most exciting two minutes in sports.” the Kentucky Derby also called the “First Jewel of the Triple Crown,”is preceded by a few weeks of really festive activities. The festival is also a place to be seen and enjoyed. The first Kentucky Derby was inaugurated on May 17, 1875 at the Louisville Jockey Club racetrack which later became Churchill Downs. Then the crowd numbered 10,000 people watching three-year-old thoroughbred horses race on the track. Last year the race attracted 150.000 fans jammed under the Twin Spires for an all-day party full of traditions that also included a fashion show..

This year’s May event is already garnering a lot of attention. People are studying the horses—and getting their costumes together. Travel agencies are promoting their packages. Hotels are filling up as the Kentucky Derby is already on people’s minds. Women will order their gorgeous hats in all sorts of bright colors except green as it’s considered bad luck – and no one wants that. Many men wear fashionable suits and bow-ties, even top-hats as they don’t want to leave all the elegance to the women. Saks Fifth Avenue even hosted a fabulous Kentucky pre-party where Louisville comes to New York City, with Kentucky-styled cocktails, live bluegrass band music, and lovely flowers.

This year we visited the event to snap our photos of the hats and mix with the media and New York City Derby lovers. It was a great celebration of Louisville,the kind of evening that made guests who hadn’t been to the Derby feel the exhilaration and want to go to the Kentucky Derby. Hat designers showcased their custom made hats. These milliners included New York City-based Christine A. Moore (CAM Hats); Jenny Pfanstaal (Forme Millinery); and Rachel and Kate (The Hat Girls).

Celebrating Derby fashion is a joy, and guests marveled at the intricate designs.One New York City hat designer said she had been to the Derby 18 times, and you could sense her excitement at going to the next one.She said she loves making custom hats for her Derby-goer customers.

With cocktails being served that were reminiscent of the American South such as Old Fashioneds and Mint Juleps, there was also of course plenty of Kentucky bourbon. We felt glamorous in the magical setting, kind of in a way like we were in Louisville. This sparkling event at Saks Fifth Avenue officially kicked off the countdown to the 152nd Kentucky Derby, which will take place on May 2, 2026, at Churchill Downs Racetrack. Visitors to Louisville who come the week or so before will also take part in all kinds of other activities, such as having breakfast at dawn watching the horses train, or joining lots of food tastings from great chefs, music and live entertainment, and many family-friendly activities.

Singing “My Old Kentucky Home,” drinking mint juleps, and anticipating the two-minute drama to see the winning horse receive a garland of red roses draped on its back are among the traditions at the Kentucky Derby. Along of course with wearing all the gorgeous, intricate hats.

Check out Kentuckyderby.com for more information. You can read about how each year 20 horses have the once-in-a-lifetime chance to run in the Derby. To earn a spot, they must travel along the Road to the Kentucky Derby, a series of races on tracks around the USA and around the world. Points are awarded to the top finishers in each race. The 20 horses with the most points earn a spot at the starting gate at the Churchill Downs in the Kentucky Derby in what’s called “The Run for the Roses.”A wonderful destination for travelers, Louisville also provides a great restaurant scene, fascinating museums (including one on baseball bats we have toured), historical sites, a beautiful downtown area, and easy to walk-to locations. The city also boasts a thriving arts and theater scene, and much more. Be sure to visit the newly-renovated Kentucky Derby Museum! Visit Louisville Tourism at www.gotolouisville.com.

Carla Marie Rupp and Jason Rupp are freelance travel journalists, reached at [email protected] and [email protected].