If you look beyond just headsets but also look at headphones (which you can use in combination with either a clip on or desk-stand mic to achieve the same thing), then there are a lot of options that do not fit as snugly, and have soft cushioned earcups. They are easy to use when wearing glasses. An example would be the Sennheiser HD518 which seems reasonably priced. It is cheaper than most high end headsets, which leaves you enough money to get a soundcard (example, Asus xonar low-mid range 40 bucks) and mic (zalman clip on 10 bucks).
Personally I like the wider range of products in headphones, the fact that you can use them for other things than just the PC, and it is easier to avoid that " gamer" look.