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Massive head: Most comfortable pair under $350
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Audio Technica ATH-AD700x (or 500x, 900x, etc. have the same structure, but I only have experience with the 700x). They are designed for big heads. I have never had an issue with fit but these were way too big for me, and the wing things are only good if you have a big head. In that case, they make it feel really light on your head. They're open backs though, so I'm not sure if isolation/sound leaking is an issue for you. I LOVED the way they sound (huge soundstage with incredible imaging) but sadly just too big for me :-(