Hm, this is actually pretty tough. Glad we're not choosing this by a vote of what really is the punkest thing. I'd so lose. I've done two Kitty hats, one was purple and pink Cheshire cat themed. The other was black and I put two of my old CBRs (from the days when my belly button was pierced) in the ear. It's pretty hot, now if only I could find it.
But I guess the real candidate for this would be the Converse Booties I knit for my baby. I modified the pattern from one I found on craftster. Ah, there's a whole post on it on my blog. Eventually I added little blue stars inside the white circles, I was just very unsure of my ability to create a decent looking star. lol The first day he actually fit into them was on my birthday, it was very exciting.