Firstly, I do not think wear a wig will make you look weird. As long as you can choose a suitable wig for your face line. Usually i will prefer short hair wig when wearing glasses if your eye glasses is framed. This match way can show an exaggerated style that always goes with modern. And if eye glasses is rimless, then you wear a long curly hair wig, it can represent white collar style.
It depends on what type of wig you wear. If you wear normal wig in usual life, you can choose some normal and common eyeglasses to enhance your look as well as provide your vision aids. But if you wear wig that for a special party or enjoy some concert etc, you need to wear some grandiloquent eyeglasses such as colored cat eye glasses or some novelty eyeglasses according to your dresses.
It will not look weird when you wear both the glasses and a wig. If you want to look so obvious, you could do the makeup to beautify the face and make the whole look balancing and harmonious. You could use the eye shadow to light the eyes which will let the eyeglasses not look that nerd.