Truly, I think the solution is to either wear biking liners, or view shorts with chamois as underwear, and wear something thin and loose over them if you prefer. I used to wear underwear under bike shorts without trouble, but once I upped my distances and tried without, there was no going back. Chafing can kill the joy of biking.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett