London hatter William Bowler is credited with making the first derby hat in 1850, which is why derbies are often called bowlers. Made of hard, shellacked felt and designed to protect horseback riders from branches scraping their heads (the felt would be of no help in a fall), the hat featured a melon-shaped crown that was much lower than top hats, the traditional riding hats of the day, as well as a rounded brim.

Derbies quickly crossed the pond and were embraced by settlers in America’s Wild West. Stetson’s Boss of the Plains may have been the first true cowboy hat, but the derby appears to have been far more common. Criminals loved them: Black Bart wore a derby, as did Butch Cassidy and his gang. But good guys also donned bowlers—the Pinkerton detectives who eventually broke up the Jesse James gang all wore bowlers.

Throughout the 19th and into the early decades of the 20th century, the derby was a hat for men. Lawrence and Hardy wore bowlers to comic effect, as did Charlie Chaplin. But by the 1930s milliners were fashioning versions of the bowler for their female customers. Some were similar to traditional derbies, save the lengths of veil than hung from their rims, while others were more radical departures, such as the shallow-crowned derbies sold by Saks Fifth Avenue. By the 1960s, Elsa Schiaparelli was making derbies in shiny yellow vinyl.

Another group of women long associated with bowlers are members of the Quechua and Aymara tribes in Bolivia. It’s not precisely clear when or why indigenous Bolivian women took to derbies, but according to one creation myth, a shipment of bowlers intended for British railway workers in the 1920s contained hats that were too small, so the hats were given to the locals. Since women had smaller heads, they ended up with the hats and the style stuck.

Today, the derby is lodged deeply in the iconography of Western culture. Belgian artist René Magritte created numerous painting of men wearing bowlers, from “Golconda” in 1953, in which it appears to be raining bowler-topped men, to “The Son of Man,” a 1964 work that depicts a man in a derby whose face is obscured by a large, green apple.

More populist is a character such as Odd Job, an evil henchman and James Bond foe in “Goldfinger” from 1964. Odd Job’s bowler featured a razor-sharp rim that, when thrown, was lethal enough to take the head off a stone statue. John Steed of "The Avengers" wore a bowler, as did Alex and his ultra-violent droogs in "A Clockwork Orange." But the derby was not always so sinister, as hilariously seen when Monty Python’s John Cleese would wear one while demonstrating a series of extremely silly walks.

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