Bose IE2

Price: $100,  

The IE2s are the cheapest pair of headphones you can currently buy from Bose. That said, they're better than the best models most brands offer. Thanks to Bose's StayHear tips, these may be the most comfortable headphones on this list. Though they're not meant for athletic activity, they won't fall out of your ear if you have to do a brisk jog to catch a train. Oh, and they sound great like all Bose products do.