mobile-bannertablet-bannerdesktop-banner
Crowds on hand the day before Kentucky Derby running at Churchill Downs, Louisville, Kentucky, 1935.
Crowds on hand the day before Kentucky Derby running at Churchill Downs, Louisville, Kentucky, 1935.Bettmann—Getty Images
Crowds on hand the day before Kentucky Derby running at Churchill Downs, Louisville, Kentucky, 1935.
Formally dressed men and women at a Kentucky Derby party, 1937.
Ms. Doris Murphy attending the Kentucky Derby, Louisville, Kentucky, 1938.
Damon Runyon Watches Kentucky Derby in 1938
Spectators attending the Kentucky Derby, 1945.
People placing bets on the Kentucky Derby, 1945.
Fans eating in restaurant at the Kentucky Derby, 1946.
Fans getting ready to place bets at the Kentucky Derby, 1946.
Seven of the Jockeys scheduled to ride in the 1947 Kentucky Derby sit on the rail at Churchill Downs after taking part in the Kentucky Oaks. L. To R., with horses they'll ride: Steve Brooks, Star Reward; Johny Longden, on trust; Eric Guerin, Jet Pilot; Shelby Clark, Cosmic Bomb; Eddie Arcaro, Phalanx; Job Jessop, Liberty road, and Will Balzaretti, Riskolater.
Jockey Eddie Arcaro is kissed by his mother, Josephine, holding roses, after winning the Kentucky Derby at Churchill Downs, Louisville, Ky., on May 3, 1952. At left is Lucille Parker Wright, whose racing stable Calumet Farm has had five Derby winners. At center is Ben Jones, who has trained all six Derby winners.
Spectators at Churchill Downs on Kentucky Derby day, 1955.
Three women sitting in the infield at Churchill Downs on the Kentucky Derby day, 1955.
Fans wait for the gates to open for the 1955 Kentucky Derby.
Waiters serve mint juleps to spectators at Churchill Downs on Derby day, 1960.
Kentucky Gov. Louie B. Nunn, right, raises his program to his face as he talks over the Kentucky Derby program with President Richard M. Nixon in the governor?s box at Churchill Downs in Louisville, Kentucky on May 3, 1969.
AP Photo
Crowds on hand the day before Kentucky Derby running at Churchill Downs, Louisville, Kentucky, 1935.
Bettmann—Getty Images
1 of 16

A Brief History of the Kentucky Derby Hat

"They'r-r-re OFF!" wrote TIME in a 1926 recap of the Kentucky Derby.

"The long roar thundered like a wave, grumbled like a rising sea-surge through the crowd down the long stretch," the piece continued. "The stands seemed to sway, to swell with it; hats and parasols and a foam of faces rose, hesitated for an instant on the top of the wave, settled slowly down into a whisperless silence. The horses moved down the stretch. It was a perfect start."

The piece, "In Louisville," contained TIME's first-ever reference to Kentucky Derby hats—but at the time, the hats were hardly remarkable. Their presence was mentioned as a given. And one look at the vintage Kentucky Derby photos above will reveal that such a situation continued well into the race's history: many women and men wore hats, but they weren't the outrageous (and often ridiculous) hats for which the race is known today.

Now, however, the grandstand at Churchill Downs is one of the rare places in America where elaborate headwear is the norm, and at the race this Saturday the hats are sure to be a focal point. How did that happen?

Get your history fix in one place: sign up for the weekly TIME History newsletter

Fashion has always been an important part of the Kentucky Derby. It was after traveling to the famed Derby races in England and the Grand Prix de Paris in France in 1872, that Col. Meriwether Lewis Clark Jr. decided to establish a similar high-profile horse race in America. He raised money for a racetrack outside of Louisville, Ky., and held the first Kentucky Derby in 1875.

Though races were a mainstay for British and French society, American women at the time might have hesitated to stay away from horse racing, and the gambling and drinking that went along with it. But if wouldn't do for the new race to seem seedy. So, in pursuit of his vision, Clark and his wife enlisted the ladies of Louisville to attend the races to picnic with friends. They knew that part of creating allure for the event would be positioning it as a fashion event — so the dress code required "full morning dress" for men and women from the start.

Fashion at the horse races, 1945.
Fashion at the horse races, 1945.Nina Leen—The LIFE Picture Collection/Getty Images
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Fashion at the horse races, 1945.
Nina Leen—The LIFE Picture Collection/Getty Images
1 of 12

The picnicking women therefore wore hats and gloves with their dresses. And though the attire has evolved somewhat throughout the decades, the hats have remained a constant. By the 1920s, though the daytime Kentucky event didn't attract much of the flapper style for which the era is remembered, the ladies could choose between formal suits or dresses to go with a range of fashionable hat styles.

In the 1960s, attendance and fashion rules relaxed a bit across the nation, and at the racetracks. As hats receded from the category of everyday clothing, the crucial change occurred: people who didn't wear hats all the time were more likely to use the excuse to wear something extreme, with bigger brims and bolder hues. Going all out became a way to gain attention and admiration.

How To Throw a 1930s-Inspired Mint Julep Party for the Kentucky Derby

A perfect mint julep expression is here displayed by Jonathan Van Dyke Norman, who critically sniffs the aroma of mint and Bourbon as he holds a silver mug somewhat defrosted by affectionate handling.
Caption from LIFE. A perfect mint julep expression is here displayed by Jonathan Van Dyke Norman, who critically sniffs the aroma of mint and Bourbon as he holds a silver mug somewhat defrosted by affectionate handling.Alfred Eisenstaedt—The LIFE Picture Collection/Getty Images
A perfect mint julep expression is here displayed by Jonathan Van Dyke Norman, who critically sniffs the aroma of mint and Bourbon as he holds a silver mug somewhat defrosted by affectionate handling.
Tall glasses holding mint juleps, consumed by Kentucky Colonels at the annual Kentucky Colonels Julep Reception held at Louisville's Kentucky Hotel day before the Derby, were pronounced incorrect by the private party guests shown elsewhere on these pages who drank their mint juleps from silver mugs.
The Van winkle kitchen was a pleasant scene of hospitable preparation as trayful after trayful of silver-mugged mint juleps were sent to the appreciative Derby Week guests.
The No. 1 Van Winkle servant, white-gloved William Kirby, expertly balances a tray of juleps with the second-nature dexterity acquired during 22 years with the same family.
Congenial celebrants at the Van Winkle mint julep party included, from left to right, T. V. Hartnett, tobacco bigwig; Mary Van Winkle, the host's daughter; Richard Dewey.
Mint julep drinker Mrs. Eugene Walker demonstrates how a Louisville belle manages to achieve maturity gracefully and happily.
Changing into evening dress, many Van Winkle guests proceeded to Mrs. Henry J. Powell's buffet supper. Above, left to right, Mrs. Rowan Morrison, Gustave Breux, Mrs. William C. Hall and Judge Arthur Peter. The tall glasses contain not mint juleps but Bourbon and soda.
1937 Kentucky Derby
1937 Kentucky Derby
1937 Kentucky Derby
Pre-eminent among Churchill Downs officialdom at the 63rd Kentucky Derby held Saturday were the four stewards of the race. Left to right they are: Sam H. McMeekin, C. Bruce Head, S. C. Nuckols and Presiding Steward Charles F. Price.
1937 Kentucky Derby
The black quartet shown consists of Churchill Downs Bar waiters. The bar overlooks the track and no Bourbon-and-soda orders whatever are filled when the Derby horses are coming down the stretch.
1937 Kentucky Derby
Churchill Downs jockeys in their quarters, include several who rode in the Kentucky Derby. At lower left is Hubert Leblanc who rode Miss Mary Hirsh's No Sir. Next to him is Hilton Dabson, who rode William Shea's and Miss E. G. Rand's Merry Maker. Fourth from left, with the number 10 on his sleeve is Basil James, who rode J. W. Parrish's Dellor.
War Admiral Wins the 1937 Kentucky Derby
Caption from LIFE. A perfect mint julep expression is here displayed by Jonathan Van Dyke Norman, who critically sniffs
... VIEW MORE

Alfred Eisenstaedt—The LIFE Picture Collection/Getty Images
1 of 16

Since then, the hats have become fodder for chatter and style watches alike. The Kentucky Derby website claims that the fashion at the Royal Wedding of Prince William and Kate Middleton renewed enthusiasm about hats, fascinators and headpieces that defy categorization. This year marks the 142nd time people will arrive at Churchill Downs under the weight and shade of their derby hats—but even Col. Clark himself could not have guessed how important the headwear itself would become to spectators of a horse race.

TIME may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.