This combo of a grey plaid overcoat and a black long sleeve shirt is a safe option when you need to look dapper in a flash. Finishing with a pair of dark brown leather boat shoes is an easy way to inject a carefree touch into this getup. Can you see how super easy it is to look seriously stylish and stay cozy come fall, thanks to this look? A look like this will make you look a million times classier as a young guy.