Headphone for sleeping recommendation?

I have some Avantree over ear headphones (two types that share the same bodyshell design) and you are right that after a few hours the ear against the pillow start to hurt. I do have some 'inner ear' style headphones as well  which are far smaller and don't pose the same problem. Maybe that sort will suit him best - especially if they're very comfortable to wear in the first place with soft ear canal cushions/buds installed.