I've been wearing glasses all my life, now edging closer to 60 y.o., and this has never been an issue with me. Yes, with cans that have high clamping force, and harder earpads, they can get irritating. One that I recall giving me some issue was the Fostex T50RP, it was quite new and the earpads were thinner, allowing the front of driver enclosure to press against the ears.
I decided that a change of earpads was in order, and it so happened that I'd sold off my MrSpeakers Alpha Dog, and had a spare pair of Mrspeakers Alpha Pads which I'd also gotten. I replaced the stock pads on the T50RP with the Alpha Pads (big soft, Lambskin pads) and the pressure on my ears with the T50RP was mitigated by a fair bit. I now have no problem wearing it for two hours or more.
Another benefit of a change of earpads is a change of sound signature, the T50RP was initially not a pair of can that I'd consider keeping (I had gotten it as my first foray into Planar Magnetic) but upon the change of earpads to the Alpha Pad, man, what a difference! Don't ask me what the difference was in terms of sound, it's been quite a few years since I'd done that, but I do recall the T50RP not sounding so harsh (prolly due to stoclk pads letting drivers press right against your ears). That's why I now have a preference for bigger and softer earpads (the Alpha Pad and Lawton Angle Pads are to die for!).
Edit - Found a pic of my T50RP with the Alpha Pads, note the size of the pads, though you can only have my word on how soft (and comfortable) they are.