From The Crown in the morning to the Triple Crown at night, May 6 could go down in headwear history. In London, King Charles III’s long-awaited coronation brought out a sea of fancy hats and flowering fascinators—Princess Anne’s feathered millinery temporarily caused Prince Harry to have an obstructed view of the festivities—while in Louisville, the horse racing faithful gathered in their Churchill Downs finery for the 149th running of the Kentucky Derby.
Dressing up on Derby Day is a tradition that dates back to the early days of the Run for the Roses. In 1875, when Colonel Merriwether Lewis Clark Jr.—grandson of the famed American explorer—helped found the race, he was inspired by England’s Epsom Derby, which had formal dress codes for spectators, including hats. Clark believed that if spectators were in “full morning dress” it would help keep away the kind of people who might only be drawn to a sporting event simply because there was gambling and drinking.
And he would have lost that bet.
Dialed Up: A Kentucky Oaks fan in full bloom.
(Photo by Jeff Moreland/Icon Sportswire via Getty Images)Because fancy headwear was already a Southern tradition, Louisvillians immediately embraced the high fashion standards and by the time the Derby was first televised in 1952, fine millinery was as ubiquitous as a fresh mint julep at Churchill Downs.
Familiar tropes always return to Louisville on the first weekend at May. Flowers remain a dominant theme with Derby dandies. Roses have been associated with the “most exciting two minutes in sports” since 1896, when the winning horse, Ben Brush, was draped in a garland of pink and white roses.
Several years years later, red became the official color of the Derby rose and spectators have been in full bloom ever since. (Pink remains the official color of the Kentucky Oaks, a race for three-year-old fillies the day before the Derby.) Millionaires Row and the infield are always filled with festive red, pink and white hats covered in bouquets of roses—or perhaps one giant bloom.
Of course, a garden’s worth of other popular flowers can be found among the Hat Pack. And given the number of julep-themed headwear every year, mint sprigs may technically count as part of an arrangement.
Winging It: Floral-themed hats are always popular at Churchill Downs.
Joe Robbins/Icon Sportswire via Getty ImagesNaturally, flowers aren't the only way to decorate a Derby Day hat—colorful, flowing feathers are a perennially popular choice, while silk, tulle, and other ethereal fabrics are always in fashion. The desire to go big on Derby Day can also mean wearing something extra-wide or sky scraping, like Churchill’s famed Twin Spires.
Some spectators get creative with their themes. Because the 149th running of the race falls on Cinco de Mayo weekend, some attendees dressed to honor both occasions. While others stuck to the basics and adorned their hats with horses, horseshoes, and other equine symbols.
One spectator even honored the great Secretariat—whose recording-setting victory at the Derby occurred 50 years ago on his way to the Triple Crown——by recreating his iconic blue-and-white checked silks.
The GOAT Horse: In honor of the 50th anniversary of Secretariat's win at Churchill Downs, one fan paid tribute to Big Red.
(Photo by Andy Lyons/Getty Images)And celebrities—always there to see and be seen—also throw their hats into the fray. Houston furniture mogul and America’s most outrageous gambler, Jim “Mattress Mack” McIngvale, paired a rose-adorned blazer with a black cowboy hat. While former J. Crew creative director (and current Real Housewife of New York) Jenna Lyons went with a black-and-white ensemble and a gauze-like fascinator.
It turns out there is also a famous horse race at Churchill Downs and the big news of the morning was that heavy Derby favorite Forte was scratched due to a bruised foot. But hats off to all the horses, jockeys, trainers and owners who competed—and would have made Colonel Merriwether Lewis Clark Jr. proud.
Thinking Pink: A Kentucky Oaks fan lets his hair down—and out.
Stacy Revere/Getty Images
