Hipster

"Hipster" originally referred to poor, black, jazz performers. It later grew to encompass blacks and whites who were dedicated to jazz and beat poetry.* They thrust themselves out of the main culture, lived in fallen-down neighborhoods and were working with new art forms.
The current use is the opposite of the former meanings. There are now "trust fund hipsters" who are making neighborhoods too expensive. If they lack money they use what is derisively called "hipster PDA's" (note pads). Most importantly it means uncool- "[someone] who derives his identity largely through his association with a subculture which has been deemed hip". The following of counter-culture music has become another example of trying to fit in.
It now reflects only on the speaker, meaning "there are people who either dress better or attend cooler events than me, and I'm better than them because that is all they care about. And that makes them uncool." The speakers also seem to be wanting recognition of their use of a "cool" word. The unremarkable "hipster PDA" is frequently mentioned in magazines and websites (22,000 Google hits). Is there anything so special about using a notepad to record events?

*Even historically "hipster's" picture is somewhat confused. A hipster "wore a beret, dressed completely in black, smoked mentholated Kool cigarettes, wore sunglasses even after sundown". This is not a good description for many of the famous ones- Lenny Bruce, Miles Davis, Ginsberg, and Kerouac.