I have always hated wearing headphones. They make me uncomfortable and sweaty and usually give me a headache. Earbuds are a lot better, although I still don’t like to wear them. However, there are lots of situations where I need headphones to play music – late at night, at work, out jogging. I would like to find a way to make headphones more comfortable, so that it isn’t such a chore to use them when I need to. I suspect that the underlying problem is a combination of ventilation, weight, pressure points, and volume (perhaps in specific frequency bands). What can help?
Ideally, I would like it if I could wear both closed, noise-canceling headphones (for work) and lightweight, open headphones (for jogging). However, there are a lot of circumstances where any headphones or earbuds would help, if only I could wear them comfortably.

How can I know if I'm damaging my hearing when listening to headphones?in regards to music appreciation. I think it should stay open. – Darrick Herwehe Feb 26 '15 at 13:48bon the side - you don't get what you pay for. I own some Phillips over-ear headphones that cost something about 40 bucks. They have a greater frequency range than most beats and only get uncomfortable after a long time of wearing them. But I guess this is a usual thing for headphones. – Alex Feb 27 '15 at 08:36