In his book Jazz, Frank Tirro defines the 1940s hipster:
To the hipster, Bird was a living justification of their philosophy. The hipster is an underground man. He is to the Second World War what the dadaist was to the first. He is amoral, anarchistic, gentle, and overcivilized to the point of decadence. He is always ten steps ahead of the game because of his awareness, an example of which might be meeting a girl and rejecting her, because he knows they will date, hold hands, kiss, neck, pet, fornicate, perhaps marry, divorce—so why start the whole thing? He knows the hypocrisy of bureaucracy, the hatred implicit in religions—so what values are left for him?—except to go through life avoiding pain, keep his emotions in check, and after that, “be cool,” and look for kicks. He is looking for something that transcends all this bullshit and finds it in jazz.
A hipster is one who would aspire to be a snob but who (unlike his bourgeois counterpart) cannot afford to signal membership in the aristocracy by donating to institutions like museums and concert halls.