Try pairing a brown houndstooth overcoat with a tan dress shirt to look like a stylish dandy with a great deal of style. As for shoes, complete this getup with black leather derby shoes. During the winter months, when practicality is everything, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a practical illustration that you totally can stay toasty and remain stylish in the winter months.