You don't have to be good looking, as personality will keep him interest. If you ARE concerned about your looks then remember, You can't judge a book by its cover. I know how awkward it can be when theres nothing to say, but the chances are a lot has happened over the summer so there will be heaps for you to talk about. Like what you got up to and things that are going on. Just a tip, don't talk to much about you, ask him how his holidays were etc. I know this is going to sound so cliche and predictable but if he doesn't like you for you, then he's not worth it. Im sure he's probably just as nervous as you anyway. And about the what to wear question, if you're going to the beach and its mean to be cold just wear something casual like some jeans and a pretty top and a leather jacket. Nothing too dressy but nothing that makes you look like you put in no effort. And silences aren't always that bad, however if it is unbearable bring up something like the olympics and the opening ceremony. You can't go wrong :) Hope this helps and good luck xx