A:Answer I would actually grab these headphones, they are very comfortable, I don't like the in ear headphones because they just fall out or make my ear uncomfortable, you can also try the type of headphones that have the around ear piece and the piece that goes in the ear just hovers or sits but doesn't put much pressure. I would think though the most comfortable ones would be over the ear like these Sony, they are cheap and the swivel piece makes them conform better.