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Are there any over-ear wireless headphones that stay cool and have ample clearance for adult ears, and well under a $100 price point?

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Have you considered bone conducting headphones? Since they don't actually cover your ears you stay cool, and if you want to block out outside noise they come with ear plugs. I wear mine constantly.

Shokz OpenMove headphones are around $80 https://amzn.to/3LgYCq8

qooqie

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I couldn’t recommend these more! The quality of the sound is top and they’re fucking awesome. Never worry about sweat making my ears slippery or anything. Also the first time you use them it’s kind of a strange experience.

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