Levi's Boys 8-20 Plaid Cargo Short, Orange Plaid, 16

Shed some layers. He'll stay stylish even without a jacket in this scholarly argyle sweater-vest from Sean John. (Clearance)

He can dress up like he's on the dark side with this Darth Vader hoodie, which includes a face mask just like Darth's.

A durable shell keeps out the elements while a soft lining keeps him comfortable, this polar fleece jacket from Nautica is what he needs when the temperature goes down.