It's a matter of personal preference.
The Tristar and Mirage are popular choices. An eyeglass accessory kit is available for the Mirage headsets, and it provides more stability for people wearing eyeglasses with the headset. The part number for the eyeglass clip kit is PN# 40700-01. (Click on the part number to view a picture.)
Other choices include our headband style headsets, such as the Encore and Supra headsets. Some people put on the headband style headset first and then slip on their glasses for a more comfortable fit.