The word is older than you think: it pops up in an old Seinfeld episode where Jerry refers to Kramer as a "hipster doofus." It even predates that by many years. A few years ago, it was convenient shorthand to refer to someone who overcompensates, who tries too hard to be unique and interesting and winds up a caricature.
Common usage, unfortunately, has utterly ruined the word's usefulness; just as "emo" came to mean anything sad, "hipster" now refers to anyone with an even slightly artistic bent.
Wearing a concert shirt from last night's Death Cab For Cutie show? HIPSTER. Found a vintage pair of eyeglass frames that were unique and you thought suited you? HIPSTER. Get bored and draw on your shoes? HIPSTER. The word has lost all meaning and therefore all usefulness.
Well, there are two sides to that coin. There's another phenomenon, that of the broseph, a.k.a. dudebro or bro-dude, which is the polar opposite of the hipster.