The story of Kentucky Derby hats — the wide-brimmed, straw fashion statements that ride into Churchill Downs each year atop the heads of well-heeled spectators — is a story of American enterprise.
Col. Meriwether Lewis Clark Jr., the founder of the Kentucky Derby, probably did not envision his success in terms of feathered hats and fascinators. But transforming the racetrack from a place of ill-repute to place of high-society—and therefore high fashion—is precisely what he had in mind.
“Gambling and drinking went hand in hand, so [the pre-Kentucky Derby racetrack] was not a place for women and certainly not a place for children,” said Wendy Treinen, a spokeswoman from the Kentucky Derby Museum.
Inspired by trips to London’s Epsom Derby and Paris’ Grand Prix — posh events that attracted an elegant crowd — Clark sought in the 1870s to transform American racetracks from places associated with immorality and vice to venues that might attract a wealthier, more noble set. With the help of his wife, he went on a campaign throughout Louisville, Ky. to convince his target clientele that the new race track was in fact a place for the upper-class.
“He loaded up a wagon full of high society women and they were going door-to-door telling their friends, ‘We’re going to have a picnic at the racetrack,’” Treinen said. “He really tried to break down this [stigma].”
At the time, the media speculated that if the track could be transformed into a place of fashion, all the investment that went into the world-class venue would pay off. And it did.
More than 10,000 spectators attended the first Kentucky Derby on a sunny spring Monday in 1875. The New York Times reported that, “the grand stand was thronged by a brilliant assemblage of ladies and gentlemen” and the center field was crammed with carriages. While it would be two more years before the first international celebrity would attend the race (Polish actress Helena Modjeska), it was viewed as a major success and paved the way for even grander affairs that quickly became as much about the fashion as they were about the racing.
“Women coordinated their hats, dresses, bags, their shoes and their parasols,” said Ellen Goldstein, a professor at the Fashion Institute of Technology. “To go to a horse racing event was really a regal affair. It was just as important as going to a cocktail party, or a ball.
“You had the middle class and lower class people who could not afford to go to a couture milliner buying off the rack. But the upper echelon, the high society would definitely be ordering in advance from Paris and from Rome and from Milan, and really looking for something that was the best of the best.”
Like today, the media took great interest in who attended the race and what they were wearing. National newspapers published dizzying lists of the notable spectators and their guests, devoting as much ink to the fashion and pageantry as they did to the race itself.
In 1925, a race marked by a disastrous downpour, the Washington Post reporter covering the Derby wrote extensively about the damage to women’s clothing before ever acknowledging the winner of the race (a black stallion named Flying Ebony).
“Leghorn hats, pink Milan hats, large white felt hats and just hats drooped; flimsy dresses clung closely to their humiliated wearers and fancy shoes soaked up more water than there was room inside them comfortable,” the reporter wrote. “When the rain finally did cease, it was all too late—thousands of dollars worth of beautiful clothing had been ruined and thousands of equally beautiful women were miserably unconformable.”
While fashion always played a central role in the Derby, the flamboyant titanic hats that have become routine photog fodder at each year’s races didn’t make their debut until the 1960s, when social fashion norms loosened up and the ubiquity of television gave women an added incentive to stand out in the crowd.
“The hats became larger, more avant-garde,” Treinen said. "Formalities dropped away, the hats had more prints, they were brighter.”
While the devotion to Derby headwear dropped off a bit in the 70s and 80s, it picked up again in the 90s, and in the last decade saw a significant surge, thanks largely to the royal wedding in 2011—an event that showcased a parade of elaborate hats and fascinators and put exclusive milliners like Philip Treacy and David Shilling on the mainstream map.
Linda Pagan, owner of The Hat Shop, a New York boutique that has made hats for the Derby for the last 18 years, says that the race has become one of the most important events for her business.
“About six to seven years ago we started to notice that April was becoming our big month, and last year April was our biggest month ever,” Pagan said, noting that those who wait until the month before the May race to order custom-made hats are actually cutting it dangerously close. “Serious race women start thinking about their outfits in February.”
The custom hat-making process is labor intensive and, as for any other type of luxury, pricey. At Pagan’s store, custom Kentucky Derby hats cost between $300 and $500 with some going for as much as $2,000.
“It takes a minimum of three weeks. Someone has to take a bundle of straw and stitch it,” Pagan said.
The emerging trend Pagan has seen, is for hats to be a bit smaller, though the traditional big brims are still the most popular choice and in demand for a string of posh races.
“There’s the Melbourne Cup, and then the spring is sort of the big season. There’s the Dubai Cup, and then you have Preakness and Belmont,” Pagan said. “Anywhere there are horses, there are hats.”