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I wear over-ear headphones with glasses for flying and the seal and comfort are fine (although they are quite warm). No problems sleeping either.
Mine are Sony wh1000xm3s - I preferred them to the equivalent Bose.
I used to use in-ears but they’re not that comfy over a long period and put pressure on your ear if you sleep on them. I’d probably switch to soft earplugs if it’s a planned sleep anyway.
For use when flying I'd say get in-ear. On or over don't play nice with sleeping and headrests. I have Bose QC 20 and even when I'm not watching a film, I just leave them in.