Most comfortable headphones

My partner stays up all night listening to the tv and music using Sennheiser 600’s. She has had the same pair for 20 years... we have an extra pair in case these wear out. She frequently ends up sleeping with them on. Kind of the definition of comfortable. The new 660s have the same form, although sonically have been upgraded are $499. Sound is outstanding.

Sennheiser 6xx. I have a dozen headphones, these are the most comfortable by far and sound great. 

Grado, they range from $80 on up. Light weight. They are all open back so not good for noisy places, just FYI. 

I have found that the Brainwavs leather upgrade pads really increase the comfort of headphones. (totally better than most stock pads).

Other than that, some headphones have a tighter clamp spring which some people complain about.

It depends on what kind of headphones he likes. If Bluetooth, you can look at Sony I have had them for 6 years, and I do not want to change. Along with them, I used wired headphones for the computer, but the wires are constantly getting tangled. And Bluetooth doesn't break as often.