Do looks matter? To what extent? I know this guy and he's "okay" looking but with a really nice style. He talks as much as I do. We are a bit similar, and he's funny! but just "okay" looking. Should that matter?
People can grow on you. Right now, you might think that he's just okay, but if you like his personality, he'll probably become more attractive as you get to know him better. And you seem to like him, so I don't think you should worry too much.
Well, *you're* the one who seems to be interested in him, so the only one who can answer that is you. It's irrelevant whether other people think it matters, because we all have different tastes and different tolerances. It's up to how much you put into physical appearance, and whether or not you're attracted to him (though it seems to me you are).