Just to followup - I posted a few weeks back about looking for a comfortable headphones.
I had previous owned DT 770 Pro 80s, which were comfortable but headclamps. (Stretching didn't seem to help much.)
So then I ordered a pair of
AKG K272 HDs. They had glorious comfort reviews, but I thought they pulled down on the top of my head harder than if they were just sitting on there due to the elastic tention on the auto-adjusting headband. Such a weird thing.
Anyway, I returned those a few days later (to Amazon) and ordered
Sennheiser HD 598s.
OMG... they didn't look like they'd be more comfortable than the AKGs, but man, they are wonderful. I guess I have a sensitive head or something, because I pretty much think everything is uncomfortable, but these are wonderful. I do sometimes wear a hat if I'll have them on all day for both the dreaded hair impression and also because it's a bit more comfortable.
Oh, they sound great too. I use them with a Fiio E10. (But, comfort is 9/10 importance to me, sound is much less.)
That said, it's hard to beat a Bose AE2 headphones for their SUPER light weight. Problem there is that the ear cups are a fake kind of leather that can sometimes sweat. Plus, they don't sound good (relatively).
Edit: I also just noticed after posting this than Amazon dropped the price $25 in the past few weeks. :-/ Great value though.