From the Chic to the Spectacular, Here Are 17 of Art History’s Greatest Hats in Honor of the Kentucky Derby | Artnet News

The first Saturday in May brings with it the Kentucky Derby, better known to some of us as “Ridiculous Hat Day.”

While for horseracing—and betting—enthusiasts the 147th Run for the Roses will bring about the year’s two most exhilarating minutes in sport, for the rest of us, it means a daylong affair of sipping mint juleps and gawking at the most elaborate and fashionable fascinators, bonnets, wide-brimmed hats, top hats, and more. 

But where pray tell did this tradition come from? The Kentucky Derby’s history with hats dates back to its very inception, in fact. In 19th-century America, horse-racing and betting had something of a sordid and depraved reputation. But Derby founder Meriwether Lewis Clark Jr. had aspirations toward a ritzier audience. He therefore decided he would try to create the posh atmosphere of England’s Royal Ascot race.

At Ascot Races, Gertrude Shilling appears in an apricot colored, feather-trimmed outfit, completed by a matching cartwheel hat, June 20, 1969. (Photo by Hulton Archive/Getty Images)

To do so, he invited a group of high society women to have a picnic at the racetrack. They in turn invited their friends. The upper-crust filled the stadium wearing their very best, including a number of elaborately made-up hats and bonnets. The tradition has grown over the years, becoming popular in the ’60s, into a competition of sorts. 

With these longstanding traditions in mind, we turned to art history to look for some creative hat inspiration. From the elegant to the extravagant, here are some of our faves for Derby Day. Enjoy!

Caesar Boëtius van Everdingen, (circa 1645 – 1650). Collection of the Rijksmuseum.

Joshua Reynolds, Elizabeth, (ca. 1780). Collection of the Frick.

Barkley L. Hendricks,  (1975).

Lucas Cranach the Elder, (1526). (Photo by Fine Art Images/Heritage Images/Getty Images)

Master of Ansbach, . Found in the collection of Thyssen-Bornemisza Collections. (Photo by Fine Art Images/Heritage Images/Getty Images)

Jacques-Louis David, (1810). Collection of the Frick.

Alice Neel, Alice Childress (1950). Collection of Art Berliner. ©The Estate of Alice Neel. Courtesy David Zwirner, New York/London and Victoria Miro, London.

Johannes Vermeer, (1666). Collection of the National Gallery of Art.

Henri Matisse, (1905). Collection of the San Francisco Museum of Art.

Sir Thomas Lawrence, (1827). Courtesy of the Frick Collection.

Anonymous Austrian artist, (ca. 1485). Collection of Museo Thyssen-Bornemisza.

Bartolomeo Veneto, (1520). Collection of Kelvingrove Art Gallery and Museum.

Elsa Schiaparelli’s Shoe Hat (1937). Courtesy of Getty Images.

British model Naomi Campbell during Vivienne Westwood’s “On Liberty” show on March 1, 1994 (Photo by Alexis Duclos/Gamma-Rapho via Getty Images)

, fashion illustration, early 1900s. (Photo by Culture Club/Getty Images)

Lucas Cranach the Elder, (ca. 1526-27). Collection of the National Gallery, London.

A Nick Cave Soundsuit sculpture shown during the Art Basel Miami Beach at Jack Shainman Gallery on December 3, 2014 in Miami Beach, United States. (Photo by Sean Drakes/LatinContent/Getty Images.)