Well, just to boost you confidence a little, you have a kind face, you have a good set of hair and you have a good smile (fake in the photo, but almost every smile is fake in a self taken picture... in mine they appear fake in almost every picture
I actually think you can make the hair and the glasses work, they give you an appearance of "tidiness" that can work to your advantage... you just have to make it contrast with the way you're dressed. I would suggest a light grey t-shirt, a blazer and a raw jeans with black shoes. Safe bet, the casualness of the hair will contrast with the blazer without being overdone by wearing jeans and t-shirt. The glasses will show that you have style but you're not trying to hard... you just happen to dress nice without putting too much effort into it and without giving up your previous style.
Just make sure everything fits correctly.