I've gone through many pair of headphones.
Issues with most headphones on the market.
- horribly uncomfortable after over an hour of usage
- very poorly designed arms which are constructed from flimsy plastic for easy breakage
- poor quality wire and/or connection
- sound coloring (my ears aren't sensitive enough to distinguish it
My last set was a pair of the first generation Bose Around the Ear, they're comfortable for about 30 minutes, then your ears tend to get sore. They also have some nice break points where the plastic connects to the metal. I got about one year out of these, original price was about $150.
I currently use the Sony MD4-XB500, they are extremely comfortable and durable, the failure points which I've seen in every set I've owned don't exist in these. They are so comfortable that I frequently forget I'm wearing them. The wire is sturdy and the connection seems durable.
If you have very sensitive ears... Sennheiser are highly recommended by audiophiles.