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Most Comfortable Over-ear Headphones?
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There are a lot of comfortable over ears. Most of the more expensive headphones are going to be pretty comfortable.
I find the Beyerdynamic DT-880 Premiums to be super comfortable. I also just got a pair of Hifiman HE-400i's, and find them to be great too. Large, soft pads and relatively low clamping force.
Open back headphones are typically more comfortable than closed back because they allow your ears to breathe a bit (I had a pair of HD-280s at a previous job, and they sounded nice but got super hot after a while).
I also tend to prefer velour pads to leather or synthetic.