Is Hipster the first term by which kids have identified themselves that was immediately an insult as soon as it was a definition?
Thinking back to all the themes of clothes/hair/music/etc there always seemed to be a grace period of a few years where it wasn't an one. Hipster seems to have immediately been an insult.
I thought it was meant as an insult towards posers, people trying desperately to be different, to stand out in the crowd, only to conform more than most by all looking alike.