Another sufferer of 'headset head' here, but I find the pain I get is right on the top of my head, under the band of the headset.
I wore my new Ray Ban 'Cockpit' shades on Saturday and had no problem with them under a standard Pooleys headset.
Edit: I'm looking at buying the Sennheiser HME 95 when I've done a few more hours - any opinions on this one?