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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.

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    There is a meta question about the act of listening to music, such as the other headphones question. Consensus appears to be that it is on-topic, so if you disagree, you should probably weigh in on that post. Also, I am not looking for a lateral-thinking solution, so Lifehacks would not be an appropriate place to ask this. – Bradd Szonye Feb 25 '15 at 20:42
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    Related: How can I know if I'm damaging my hearing when listening to headphones? – but I am concerned here about short-term discomfort rather than long-term health. – Bradd Szonye Feb 25 '15 at 21:00
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    No this is not a music related question. Same as if I asked "Which speakers would look best in my living room?" – user3169 Feb 25 '15 at 22:45
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    Sadly this is off topic, for sure. If not because it is not directly related to music, then because it is a very broad subject. Also more comfortable is fairly opinion based. So yes, off topic. I agree with you though that making headphones more comfortable would be nice. Maybe don't buy crappy cheap ones :/ You get what you pay for, professional headphones can cost hundreds of dollars. – veryRandomMe Feb 26 '15 at 12:14
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    I think this question has the same usefulness as 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 13:48
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These devices are based on statistical dimensions collected from various age-group/gender/activity based studies. Of course there are always outliers if the commercial risk is acceptable for the company to leave individuals like you. They also try to introduce some mechanical degrees of freedom however you don't get a lot of over-ear cover shape modification options.

What might be happening is that your ear shape lies somewhere in between two standard sizes of over-ear pieces. Moreover as I have witnessed with a few friends, your ear canal might also be shaped in a way that in-ear headphones don't stay but tend to fall.

Either way, I think you can consider the combo ones which were available in the late 90s (I think Sony had a few) but apparently they are getting hip again and I don't know how to call them, e.g.,

enter image description here

This is particularly useful because it doesn't have the in ear or over ear piece problems. It made the friends mentioned above quite happy.

As a personal note, I would also prefer using ear plugs instead of noise cancelling headphones and not listening to anything. And using headphones just for listening not cancelling the noise around you.

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