So I have a pair of of Sennheiser HD 497s that I got for about $30 two years ago. I love the sound quality with these things, as I hadn't been exposed to any quality audio with my standard ear buds. I suddenly felt like the music had much more depth to it, like it was a combination of instruments being played in harmony more than just a solid wall of noise coming through the headphones. I love them, but they are too bulky, they aren't streamlined enough for my usage. Also, they hurt my ears after prolonged use. (as in, they press on my ears causing physical discomfort when I remove them, I don't mean ear-drum pain) I feel it is time to upgrade to something in a fully over-the-ear style. Since the HD497 just dont look "cool" when I wear them because they are bulky on the sides. (I have kind of a bigger head?) What would you audiophiles recommend for under $100. if you really convince me I might be willing to spend as much as $150 or $200. Something that still looks... cool? (No skull candy though... I have never used them, but the brand bothers me) Obviously quality is more important than asthetics, but it wouldn't hurt to look good either. Also, for on-the-go use, I still use the Apple ear buds for convenience(throw them in a bag or pocket) despite them sounding awful . What would be a good choice for buds that are higher quality, but cheap enough (under $35?) that I wouldn't be too shattered if I lost/broke them? maybe something in a Senn. CX400 flavor or something? Thanks!