I've been engaged in the "nightmare" that is the headphone rabbit hole for about the last year now. I really like the M50x, which in recent times seems like it has become the most polarizing pair of headphones. I'm not entirely sure why. I've also really enjoyed the Takstar Pro 80/Hyper X Cloud, it's surprisingly comfy and good-sounding at its rock-bottom price.
I have a giant head and I wear glasses, so headphones are pretty tough for me to enjoy, especially for more than an hour. Comfort is the top priority, and I've returned a few pairs because they didn't fit my silly head correctly. Getting a good seal with my head size and glasses can also be tough. The Sennheiser Urbanite XL was the worst in this regard. It fit over my head just fine, but the cups were so bulbous and stiff that they didn't seal against my face properly, which has a more average size compared to my head.
So far, the nicest-feeling headphones I've worn in the more expensive range are the Sony MDR-1a and the Bose QC 25. I could wear both for days and feel fine. Just some random thoughts from a big-headed headphone user!