Many of us associate the fedora with the Herbert Johnson creation worn by Harrison Ford in “Indiana Jones” or the rumbled felt hats that covered the sweaty heads of Jake and Elwood in “The Blues Brothers.” But the fedora had its debut resting on the curly locks of Sarah Bernhardt, who wore a sportier version of the famous chapeau in a late 19th-century play called, appropriately enough, “Fedora.”

In fact, it wasn’t until the 1920s that the fedora—a medium-wide brimmed felt hat with a pinched-in front and a crease down the length of its crown—became associated with menswear. Gangsters were some of the first men to claim fedoras, which were produced in a palette of colors that would do a peacock proud. Today, period photographs of these stern underworld types, struggling to project an air of respectability beneath their outsized hats, appear more than a little bit comical.

As it turned out, the funny pages were actually a good place for the hat, especially when worn on the head of comics crime fighter Dick Tracy, whose yellow felt fedora, trimmed with a black ribbon, was the character’s signature.

Hollywood also took to the fedora. James Cagney wore one in the 1938 gangster film “Angels with Dirty Faces,” as did co-star Humphrey Bogart. Costume designers subsequently put a lot of fedoras on Bogie’s head. In 1941, he made the hat famous in “The Maltese Falcon,” combining it with a long trench coat to create a pairing that remains classic to this day. Bogart also wore the hat the following year in “Casablanca,” most famously when he bids Ingrid Bergman adieu in the film’s climactic airport scene.

Another celebrity to favor the fedora was Frank Sinatra, who was often seen wearing a “Stingy Brim” Cavanagh throughout the 1940s and into the ’50s, when the hat’s popularity began to decline. Even Sinatra switched to a smaller pork pie, which was thought to be more flattering to his small frame.

During the middle of the 20th century, lots of hatters made fedoras, but a few elevated the form to an art. Borsalino of Italy was clearly one of the best. Borsalino felt hats were made out of pressed fur (hare, rabbit, muskrat) rather than wool, and the hats were blocked, reblocked, and shaped with exacting care.

Before Harrison Ford tapped Herbert Johnson for his hat in “Raiders,” the London-based company made hats for the British armed forces—from Bombay bowlers for Kitchener's troops f...

Cavanagh not only made hats for Sinatra, but it created an edge for felt hats of all types. Known as the Cavanagh Edge, this rounded rim can even be found on the hats of Cavanagh competitors, from Borsalino to Stetson.

Which brings us to Stetson. Though long associated with cowboy hats, Stetson has also produced several styles of Stetson hats, which today go by names like Whippet and Benchley.

Today everyone from guitarist Carlos Santana to trumpeter Wynton Marsalis to rapper Kid Rock to football and baseball star Deion Sanders wear fedoras. Sanders is such a fan of fedoras and hats in general that he leant his name to a line of felt hats made by Dobbs.

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