It really depends. A good pair of headphones can be had for big discounts used. For in ear headphones, you can usually buy replacement ear pads and for over ear, you can often replace the foam that goes over your ear. I would never buy a lower quality pair, but I've bought a few different high end headphones that I scored on.
Regarding the two examples given (https://s3.amazonaws.com/pix-media/TV+Categories.png): used headphones are icky and cellphones are distorted by cell phone plans that hide their real cost.