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.


Best of the Web (“Hall of Fame”)

Des Chapeaux

Des Chapeaux

A French tribute to women's hats and other headwear from the 1940s... primarily magazine images, with some commenta… [read review or visit site]

American Hatpin Society

American Hatpin Society

Who knew there was so much to hatpin collecting? This site is all about great hatpin images - from recent hatpin co… [read review or visit site]



Clubs & Associations

Most watched eBay auctions    

Antique Stetson Nutria Fur Felt Derby Bowler Hat Size 7 3/8 M. Rothshild Design Black Wool Man Women's Cloche Fold Brim Bowler Hats Derby Roll Up Cap BillycockVtg *tress & Co.* London Brown Bowler Riding Derby Hat England Men's 7-1/8 (a38A256 Black Vintage Style Woman Felt Wool Floppy Derby Hat Wedding Church B047 Navy Blue Women Kentucky Derby Wide Brim Wedding Church Beach Sun Hat LinenBlack Autumn Winter Lady Men Fold Brim Billycock Round Crown Bowler Derby HatVintage Prewar Black Bowler Hat 7 3/8 1/4 Tall Crown Derby Shannon & Sokup Co.Vintage Bowler / Derby Hat By Knox Of New York Size 7 With Box ExcellentMichael Kors Signature Mk Logo Scarf Beanie Hat Set Gray Derby WomensDark Blue Lady Girls Wide Large Brim Fold Summer Beach Sun Straw Beach Derby CapVintage Dobbs Derby HatWoman's Anjulie Church/derby Hat Ashro New With Tags (see All Photos) Yellow Elegant Women Wool Leather Buckle Round Flat Bowler Derby Sun Bucket HatBlack Bowler Derby Cowboy Gangster Cap Fedora Trilby Felt Jazz Hat Ribbon Band Fashion Black Unisex Wool Parent-child Bowler Fedora Hats Derby Cat Ear Cap Free Ship Wide Large Brim Floppy Fold Summer Beach Sun Straw Beach Derby HatAutumn Wine Unisex Wool Parent-child Bowler Fedora Hats Derby Cat Ear Cap New Unisex Retro Fedora Style Hats Blower Jazz Hat Trilby Derby Cap Topper BlackNew Unisex Retro Fedora Style Hats Blower Jazz Hat Trilby Derby Cap Topper BlackStetson Hat Bowler DerbyKentucky Derby Women's Hat-redWomen's Ladies Dress Wedding Hat Wide Brim Derby Gauze Hat Church Tea Party HatWinered Bowler Derby Cowboy Gangster Cap Fedora Trilby Felt Jazz Hat Ribbon BandRed Wool Man Women's Cloche Fold Brim Bowler Hats Derby Roll Up Cap BillycockHot Unisex Retro Fedora Style Hats Blower Jazz Hat Trilby Derby Cap Topper BlackPink Lady Girl Wide Large Brim Fold Summer Beach Sun Straw Beach Derby CapRose Red Lady Girls Wide Large Brim Fold Summer Beach Sun Straw Beach Derby CapVintage Beaver Hats Mens Gray Cooney Imported Fur Feather & Owl Pin Derby HatNew Blue Wool Man Women Cloche Fold Brim Bowler Hats Derby Roll Up Cap BillycockNew Red Bowler Derby Cowboy Gangster Cap Fedora Trilby Felt Jazz Hat Ribbon BandNoble Purple Wool Hat Lady's Party Bowler Derby Hat Cloche Ddp5White Child Kids Girl Derby Cap Wide Large Brim Summer Beach Straw Sun Hat HotBeige Lady's Wide Large Brim Floppy Fold Summer Beach Sun Straw Beach Derby HatYellow Child Kids Girl Derby Cap Wide Large Brim Summer Beach Straw Sun Hat HotBlack A206 Occasion Organza Women's Kentucky Derby Hat Wide Brim Event ChurchPink Organza Wedding Dress Hat Kentucky Derby Hat Women Wide Brim Church Hat New Chic Formal Elegant Sexy Black Sun Floppy Derby Church 6" Wide Brim Hat 1szNew Hot Classy Summer Sun Beach Floppy 6" Wide Brim Bow Band Derby Hat Black Theatre-reenactment~costume/play~tea Parties~kentucky Derby-style-newly Made1pc Red Fedoras Women Trendy Bowler Top Hat Roll Brim Derby Felt Dome CapXl Green Leprechaun Derby W/white Hat Band In Time For HalloweenSky Blue Lady Wide Large Brim Floppy Fold Summer Beach Sun Straw Beach Derby HatVintage Ross Hatters London Jess Applegath Black Derby Bowler Hat Size 7 1/4"Vtg 40 50s Woven Straw Wide Brim Tilt Cloche Bucket Garden Party Derby Dress HatBlack Lady's Wide Large Brim Floppy Fold Summer Beach Sun Straw Beach Derby HatPink Lady's Wide Large Brim Floppy Fold Summer Beach Sun Straw Beach Derby HatPink Child Kids Girl Derby Cap Wide Large Brim Summer Beach Straw Sun Hat HotBlue Child Kids Girl Derby Cap Wide Large Brim Summer Beach Straw Sun Hat HotHot White Womens Ladies Wide Large Brim Summer Beach Sun Hats Straw Derby Cap C