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Massive head: Most comfortable pair under $350
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I've found some of the most comfortable closed headphones I've worn are the Denon DXXXX series, and you might be able to find some used Denon D2000 in your price range. The problem is the Denon DXXXX series is hard to find because they are discontinued and highly regarded....so people tend to hold onto them.
If you are willing to go up just a bit, you could look at the Fostex TH-X00 series, or the E-Mu Teaks that are currently available on a drop. They both use the same build style and headband as the Denon series, so should have a similar comfort level.
I have the D2000 and they are great and I can wear them all day long with no issues. I'm waiting for the TH-X00 Ebony's (they won't ship until Nov), but am really looking forward to getting those on my head! Might be looking to sell my D2000 at that time if they are too similar....we'll see.