Hi Mark, thanks for reading my stuff, I really appreciate it!

I review every single headphone and headset wearing my glasses nearly the entire time, save for one small test I do for a few minutes to see how much effect my glasses have on the seal of the headphone and the sub-bass response. So, my comfort impressions always include my personal glasses in the assessment.

In general, I find that over-ear headphones and those that use memory foam in their pads are the best bet. I don't like an on-ear fit all that much without glasses in the mix, and with them I find that almost every on-ear pair starts to pinch inside of an hour.

I've had excellent comfort experiences with too many headphones to easily list or to try and pick a "winner" from in the scope of an article comment.

Bose's QuietComfort35 is the safest choice that immediately pops to mind. HyperX's memory foam conforms well to my glasses, and their Cloud Mix is a solid Bluetooth option in a smaller frame design. In the budget arena, I had impressive experiences with TaoTronics headphones' padding, though their sound quality tends to be all over the place.

I can only test products with my specific head and my specific glasses, so everyone's mileage will vary. If you can buy from a place with a good return policy, that can help with the search.