I can't say I've ever had trouble with wearing noise cancelling headphones. I wear a pair every weekday for about an hour or so while I walk outside (my walking

I can't say I've ever had trouble with wearing noise cancelling headphones. I wear a pair every weekday for about an hour or so while I walk outside (my walking path is right next to a highway and the constant sound of cars zooming by makes it very difficult for me to relax), although admittedly they're a much cheaper pair than Bose. Ear fatigue itself is something I'm intimately acquainted with, however. I have a couple of daily cans I use around the house, all over-ear, and pretty much none of them can stay on for more than an hour or two without causing my ears some level of discomfort. I don't know how anyone can stand on-ear headphones--those are agony after just 15 minutes or so. Maybe I have large ears.