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Massive head: Most comfortable pair under $350
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Perhaps you could try out the Philips Fidelio X1 or the X2. They are comfortable and have decent soundstage. They are open-back headphones, but they sure have that "fun" sound thanks to the mids and bass they provide. They have an adjustable headband, which I never had any issues with, but just wanted to let you know. You can definitely research more on these two headphones. The X1 does not come with replaceable ear pads, so you may want to consider the X2.
Here is a 3 page review from headfonia for the X2 (which even the reviewer wishes the HD600 sounded like these headphones):