Let me try to give my points to you. Wearing beanie with glasses, some people will say, if the assorted paparazzi will run after you? Why you hide yourself so tight? If they are not suitable well together or matching you well, it will be very strange for the look. However, as for the beanie, you would choose a tiny and light colored one with some fashion pattern on it. As for the glasses, choose an exquisite and stylish one which is the same style with the beanie, no matter the color and the pattern. The glasses with dark colors will give the expression of seriousness to the people around you. If you are a lady, some makeup of blusher and lipstick will increase the outstanding beauty with mysterious and cool feeling when you wearing the beanie with glasses.
It depends on your personal preference. Here, i can give you some suggestions. If you want to get a harmonies look, you shall choose a small eyeglasses frames when you wear beanie. Do not choose eyeglasses with big frames since the beanie has cover part of your head. You'd better avoid big glasses to cover almost part of your face. So, you shall choose some small buy exquisite eyeglasses. It will make you look elegant but also harmony. Hope this can help you.
If you want to wear a pair of glasses to match with your beanie, you could choose the big frame eyeglasses. Usually the black color or the white color will be suitable which could be matched with all color of the beanie. This matching way is so fashionable which will make you look cool. You could have a try on such match.
I think you are very interested in making yourself up! That is amazing since lots of girls don't have a rough idea of what to do with their images. Anyway, I think beanie does not impede your glasses, you could just choose a pair of cute and beautiful glasses from an optical store such as Walmart vision center or a local shop, then try to make sure the color of the glasses are compatible with your beanie , and also pay attention to how you dress up, that matters too, that then you are gonna be a princess.