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Massive head: Most comfortable pair under $350
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Nothing will beat a used HD700 for comfort under $350... simply one of the most comfortable headphones ever made. Not sure how big a head it will fit though. From the cans I current have or have had/used, both the SHP9500 and K7XX are a close second but definitely not as comfortable. Then further down a used TH-X00 with ZMF Ori pads, Monolith M1060, then HD6XX. Have a Koss ESP950 coming in, their stock comfort should be somewhere between that of HD700 and SHP9500... but maybe surpass HD700 with the Vesper pads?