Comfortable shoes. He won't even look at them. Whatever you want as a top. If you have a knee high skirt go with that. That way he can put his hand on your leg in the movies. Perhaps a cardigan. He's there for you, what you wear isn't going to change that.
i prefer a girl whos taller than me with heels on. I'm 5'8".
something casual, but a little more high maintenance, because guys appreciate when you look like you tried even a little bit. so wear casual shorts, and a cute babydoll top. do your hair how you normally wouldn't, acessorize with a belt. necklace, earrings, orr headband (choose one) , find some nice shoes and you are good to go.