I like my Corsair Vengeance 1500 headset very much. It's an extra large over the ear style that is actually too big for some people, but I find them very comfortable. They can be found for $50-80 depending on the sale and location. As for one side always breaking... is it the side that you most often pull away for a few seconds so that you can hear someone talking in the room? If so, then that may be the reason, since I've had the same thing happen to me before.
After looking around a bit, I think I will go for the vengeance 1500 (or a kraken). When I can find it on sale that is. Now that you mention it, it is always the side that I pull away to hear someone (which happens often) that breaks. Huh. I never thought that might be the reason, I didn't think these things were that fragile.