the jack itself, is it a 90 degree angle or are they straight? I find that if I have the straight jacks they bend and warp the wires and I have the same fate as you. sony made a fantastic new brand of earbuds and headphones called PiiQ and they have bent jacks and great quality, really last a while too. $15-$30 at best buy. ultimately probably just from heavy use, not directly the device itself