The Beat Generation and then the Hippie movement tried to pick up this stand of thought and way of life in the mid twentieth century. The existential hero who is cool and detached, not caring what anyone else thinks of him is also a mid century fashion that picked up on this theme.
The cool hipster assumes a persona of crass selfishness, irresponsibility, mindless rebellion, cynicism, ironic mocking of anything meaningful or noble, cold reserve, uncaring indifference toward others while paradoxically advocating a politics of compassion toward certain groups favored by leftists, a dull, dumb countenance, and most of all, being constantly out of sorts--a real sour puss. They usually take on a studied disheveled appearance to further the affection of not caring what others think of them. They also prefer to dress in black.
Of course, most of these folks are as phony as you can get. They look as though they are dead on the inside--enthusiasm or being earnest or being genuine are completely missing from their emotional repertoire. They shun kindness,loyalty, spirituality, or empathy as uncool.
The surest sign of a hipster is their dislike for everything corporate so while they may never want to buy anything from a Starbucks, Gap or Pottery Barn, they will have no problem working for them since they always seem to be flat broke and complain about having financial problems, even though they have mom & dad paid BA.
Note: Hipsters dislike the title of hispster and are irritated to be called one.
Hipster: The Shins suck now for letting their song be on that album, how dare they try and make a buck.
Person: you’re such a typical Hipster
Hipster: I am NOT a hipster!
Often use the word "contrived".
Female hipster: "You're in more than one band? Let's make out."
Male/Female hipster: "You drink pino grigio too?!?! Let's make out."