I wear glasses and I have yet to find a pair of sufficiently isolating headphones that doesn't become painfully uncomfortable after 1 hour. And I've tried various high-end solutions.
Tried Etymotic earbuds? They come with a bunch of adapters to fit different sized ears. My model is of course discontinued but the mc5 looks closest. http://www.etymotic.com/ephp/mc5.html
edit: unlike any other earbuds I have tried, they are engineered to survive the inevitable wax-plugging. Just replace the filter & you're back in business.
