The term itself was coined during the jazz age, when "hip" emerged as an adjective to describe aficionados of the growing scene. Although the adjective's exact origins are disputed, some say it was a derivative of "hop," a slang term for opium, while others believe it comes from the West African word "hipi," meaning "to open one's eyes."Nevertheless, "hip" eventually acquired the common English suffix -ster (as in spinster and gangster), and "hipster" entered the language.

"Hipster" has been used in sometimes contradictory ways, making it difficult to precisely define "hipster culture" because it is a "mutating, trans-Atlantic melting pot of styles, tastes and behavior." One commentator argues that "hipsterism fetishizes the authentic" elements of all of the "fringe movements of the postwar era—beat, hippie, punk, even alternative rock,"

The term "hipster" is now mostly used as a term of derision against those whose tastes in clothes, music, and other media are perceived as pretentious and/or conspicuously and deliberately obscure. Some cultural commentators who attempt to define the concept further also stress the role of ironic juxtaposition in the so-called 'hipster aesthetic', and may provide lists of brands, behaviors, and locales believed to be favored by hipsters generally. In rare instances the term is applied positively, but for the most part it is employed as an insult.

The word was probably coined at some point in the 1940's to describe ardent fans of hot jazz music (described as 'hip', meaning 'chic' or 'knowledgeable') and its perceived attendant lifestyle.