My basic attitude is that if you think of yourself as being either "hip" or "punk" and it's reinforced by your tastes in anything means your not. The people that truly are, get there by being themselves not by setting trends, trying to be ironic, or anything else. In general society comes around to thinking that they happen to be is cool for a while (while they were on the fringes, and probably despised as rejects before), and then tends to move on while they stay where they were before hand.
I'm about the least hip person out there, but I guess to play the game I'd have to say that being a fan of Extreme Horror and Bizzaro fiction fits the obscure bill. Most people even in geek circles seem to have no idea who people like "Carlton Mellick III" are for example. Despite being fairly prolific, guys like Edward Lee, Bryan Smith, etc... have yet to creep onto the mainstream radar very often. As far as things that are popular that I hate... not much really. There are plenty of things I dislike to the point of avoiding them, but as a general rule if I dislike something I avoid exposing myself to it so it never turns into a bona fide hatred.
I've never really gotten into the meat of the whole "Ironic" thing that is a pre-requisite for being a modern "hipster poseur" nowadays. I don't consider liking something that is campy, absurd, or trashy (so bad it's good) to be the same as ironic appreciation. To be honest it seems to me MovieBob is right on the money (which happens a lot with him) when he simply says that people who claim "ironic appreciation" do so simply to avoid being mocked for something they like. While I'm not above occasional embarrassment, I just can't see the point of going through that much effort.