Thelonious Monk and friends outside Minton’s Playhouse in New York
musicians’ liberal and carefree lifestyle, adopting their fashion, streetwise attitude and even their slang. These ‘white negros’ (as Norman Mailer called them in his book of the same title) absorbed the frenzy of live Bebop like an addiction, with performances usually confined to small bars, intimate clubs and cellars, played by a small combo of saxophone, trumpet, double bass, piano and drums. Its addictive adrenaline spread from East Coast New York to West Coast LA, led by its figureheads Charlie ‘Bird’ Parker, Thelonious Monk and Dexter Gordon. Lester Young was ‘The Hipster’s Hipster’; Dizzy Gillespie was its sartorial ambassador. Recognised for his cosmopolitan style, Trumpeter Gillespie’s signature beret became a Hepcat talisman. Worn for practicality, not only for stuffing into a pocket for safekeeping, having lost numerous hats, but also, on occasion, providing an adequate mute for his trumpet. Gillespie’s creative flair and sartorial influence was infectious. A photograph of Dizzy with his fly undone (accidentally) spawned an overnight trend for ‘flying low’. He also endorsed fashion brands
such as Fox Bros, who produced several accessories imaginatively labelled ‘Bop ties’, ‘Bop caps’, ‘Bop crushers’ and berets. They even manufactured a copy of a leopardskin jacket after Gillespie had worn one. Billy Eckstein, another fashion pioneer of the Hipster milieu, created the ‘Flex roll collar’. Dubbed The ‘Mr. B Collar’, it had an expandable high-roll collar, allowing for the swelling of his neck while playing the trumpet. The collar formed a letter B, worn over a Windsor-knotted tie, and assured the wearer he could achieve ‘The Mr. B look’. Jazz singer Babs Gonzales sported the ‘Jazz bow tie’ designed by his then girlfriend. It was the size of a king-size cigarette and was little more than a piece of cloth over a sliver of wood. Despite the few musicians setting sartorial standards, the definitive insignia of the coolheaded, confident hipster was the porkpie, fedora hat or beret, worn with dark rimmed glasses, pinstripe double-breasted suits and a neckerchief. The intention was never to create a fashion statement – that would have suggested triviality and sensationalism. These artists took themselves seriously, with an
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