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Answer:
HIPSTER
Possible Questions:
Cool cat
Jazz devotee
No square
Bebop aficionado
Wearer of skinny jeans and big-rimmed glasses, perhaps
Type who wears tight-fitting jeans and thick-rimmed glasses, maybe
Trendy one
Style appellation thrown around a lot, almost never in self-identification
Smart cookie
One who runs a cassette-only record label, probably
One parodied on "Portlandia"
In type
Hardly a square
Beatnik's cousin