The associations with this very word aren't very good, but I have no idea why. In a poll at my school, people would rather be "hypesters" than "hipsters". I think the idea of being a unique individual, no matter what others say, is something very important and dear to me. Following the trends too much is not admirable in my opinion. Individuality, and creating your own style, are things that are much more admirable. I always root for the outcast, the loner, the one who isn't accepted because of some unusual trait or fact because those are the people who truly value being their own person. I don't know what the obsession with the word "hipster" is. I hear it used on a daily basis, describing someone who doesn't follow what everyone else is doing, or what they should be doing. The negative connotation is one I don't really appreciate. Its just another stereotype built to break people apart even more, and categorize every single human being into a single word.
So here's for all those people who dare to be different, even when other people try to prevent their individuality from breaking free.