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Massive head: Most comfortable pair under $350
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HD598s could be good, but HD600s and HD650s are made of a more rigid plastic.
You may want to try something like the AD700x (second time today I've posted this, swear I'm not an AT shill guys). I also have a massive head (can't fit snap backs even on the last snap) and always found AT's "3d wings" (weird two part headband thing) was the most comfortable headband solution.
Surely At this price range, the original poster should consider the AD900x and 1000x, no? I believe they all have approximately the same build except for material changes.
EDIT: I should have read the rest of the posting.. Oh well. Maybe someone else would benefit from this question. Cheers!