I listen to my iPod at least four hours a day. It not surprising, then, that I generally wear out headphones on an annual basis. On my way to Cape Cod for Memorial Day weekend my Bose earbuds just quit working on the left side. The right side got uber loud to compensate, and you can imagine my mood was shot for the rest of the bus ride. I *finally* went to AC Gears to get a new pair, and I LOVE them! I have a hard time with earbuds because my ears are small. I love big headphones (I used to have these by Zumreed) but they double as earmuffs and in the summer heat, that's a no-go. I found a very happy medium, sticking with the Zumreed brand which I've come to love (my last pair was destroyed when my kitten shredded the cord). I bought the Airily wire headphones and am in love. They deliver sound quality equal to their larger counterparts but are much more lightweight, and are a snugger fit so they'll stay put when working out.
Since they were only $36 (plus I saved 10% by checking in on Foursquare!) I got this Zumreed iPod speaker as well. I've been wanting a small, portable speaker for ages and this one is awesome.
Simple volume control (you twist the pink side of the pill in either direction) and no batteries or recharging. Score for sweet purchases and getting the music back in my day!