A classic chillz is one who is an outcast and is a real tight man. He usually has strict parents and is often rich as fuck. A classic chillz enjoys relaxing (chilling) but not ordinarily, it has be something that he has done before, hence, classic. For example, selling boom phones or playing with a yoyo are examples of a tight man, or an outcast.
Person 1: I'm kinda bored as fuck, what do you wanna do?
Person 2: let's classic chillz, it would be such good times
Person 1: I'm down, but I don't want to be treated like an outcast
Person 2: don't worry, I have the situation under control, let's just classic chills already!