<p>I would wait until he gets to Chicago, the seasons change and he figures out what he needs and WANTS. Most of what you are talking about kids around here wouldn’t be caught dead wearing :D. Many kids never put on a winter coat except if they are going skiing/snowboarding, especially if they are just going from one building to the next (not sure which school or campus you are talking about). I know plenty of kids that wear Van’s all year round. It isn’t the arctic circle and while he will have to adjust to the cold, it isn’t as bad as you think.</p>