Yeah, I understand you because I am a girl who is nearsighted. Also, I often wear the headband. You know that wearing headband with eyeglasses looks very cool. And as to your question, I think the answer will depend on the type of your headband, that is to say, if the headband is plastic, then you can just do it---put your headband first and then put on your eyeglasses, which will make you find it easy to put off your glasses when needed. At the same time, if you want to wear the soft, like cloth, headbands, then I think you can do it as the plastic headband, but there is a point you should remember that is you should be careful because the cloth headband is a little hard to put on without the vision help from the glasses. Besides, if your loved headband is complicated, you had better choose the simple type eyeglasses. Also, if the headband is simple, you should choose the complicated glasses to fit your headband. Hope my ideas help you.
Yes of course, wearing headband will definitely enhance your looks. So, I could not figure out what problems you may have in the course. My advice for you is to wear your headband in the first place, when it is done, you should just put on your glasses, typically, there will be no contradictions between these two things. I personally suggest that you leave a short bob which could perfectly suits your glasses.