Comfort is paramount when using VR. All supported headsets have various straps that allow for adjustment to a wide-range of head sizes and shapes. We highly recommend you spend as much time as you need to fully understand how your headset can be adjusted, and once you find a proper fit, make sure you adjust the headset to that fit if necessary before every use.
Wearing glasses inside the headset can be uncomfortable, as it can pinch the frames near your temples. Also, depending on the size of the frames, they may not fit inside the headset. Even if they do, they can scratch the headset's lenses. Because of these limitations, we recommend you avoid wearing glasses in the headset if possible.