There's also the fact that when you really get "into" the music and start moving your head, there are basically two scenarios: you either get the "hum" of the headphones moving on your ears, or the headphones stay put but the clamp is so tight that you can't stand them for more than 10 minutes.

I never really liked wearing headphones as well. I've setup my room such that I can use the big stereo speakers plus a decent mic (Samson Go Mic) for voice chats.

However, Sennheiser HD650 are a pleasure to wear. Even for longer periods of time. I use them with a bluetooth+USB DAC/amp (Fiio Q5; outdated) and a short cable; so I'm pretty flexible how I can use them.

Try good half-open cans like Beyedynamic DT880. I can wear them all day.