In the 1940s and 1950s it meant beatniks, bohemians, people into jazz and poetry, pushing the extremes when it came to sex and substance abuse, etc. etc.
Today it means what poseur meant in the 70s/80s - an insult for pseudo intellectual young people who claim to be into obscure pop culture of the past and are into co-opting cool stuff, and adopt white trash chic like trucker hats or Pabst Blue Ribbon, While being a 21st century hipster is preferable to being a gangsta, wigger, or yuppie, it's still nothing to be proud of today.
There is a book called "The Hipster Handbook" that made up fake "hipster" slang thinking that someone would fall for it
The only thing in common between the hipsters of the mid 20th century and those of today is that both are associated with New York City
Jack Kerouac was an example of a 1950s hipster.
Julian Casablancas is an example of a 21st century hipster
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