I wouldn't so much say it depends on the person as much as it depends on the glasses. I think everyone can find a pair of glasses that looks good on them.
Yeah. If they wore glasses the first time I met them, and they have a great personality..that's great! It honestly bothers me when the cute girls with glasses get contacts. Unless that's their preference. Enough said, doesn't matter about looks, sometimes XD
I like it. Especially if they wore glasses when I first met them. When someone you've always known as not wearing them, then wears them, it takes some getting used to.