I often have clients ask me if they should wear their glasses or not. My opinion is that if you wear your glasses often, you should wear them in your headshot. Some photographers worry about glare and reflections from glasses but I've rarely run into issues with it. My lighting setup seems handle eyeglasses without issue as Shirley is demonstrating here. You also get to see her sense of style come through in her choice of frames, which are pretty cool. If anything the eyeglasses here augment this image of someone who is already has a great look and wonderful engagement with the camera. 

 shirley