What to wear?

Well, they do pass on remarks to you, depending on what you're wearing, and for some missions you need to be dressed appropriately like for one of th preppie missions, you need to get clothes from one shop to dress like them and also change your hair, but I'm sure you know that one. Besides that, I think it might make a difference if you try to make out with a girl or something, and people give different remarks to you depending on how you're dressed.