Fedoras became widely associated with gangsters and Prohibition, a connection coinciding with the height of the hat's popularity between the 1920s and the early 1950s.In the second half of the 1950s, the fedora fell out of favor in a shift towards more informal clothing styles, though Greasers wore the hats with their leather jackets and jeans.
Coach Tom Landry also wore the hat while he was the head coach of the Dallas Cowboys. It would later become his trademark image. A cenotaph dedicated to Landry with a depiction of his fedora was placed in the official Texas State Cemetery in Austin at the family's request.In addition the Cowboys wore a patch on their uniforms during the 2000 season depicting Landry's fedora.
By the early 21st century, the fedora had become a symbol of hipsters, and later men's rights activists, internet atheists, and so-called “white knights,”, although the latter three groups often erroneously refer to trilby hats as fedoras. Vice has referred to the early 2000s, as a "fedora renaissance", with celebrities like Johnny Depp and Pete Doherty wearing the hat, but claimed that by 2016, the fedora may be "the single most-hated fashion accessory money can buy". During this latter period, James Toback was noted for his love of fedoras.