Why not rock a sweatshirt with black chinos? As well as totally functional, both of these pieces look awesome when paired together. If you wish to effortlessly dress up this getup with one single piece, round off with a pair of black derby shoes. In the winter months, when warmth is crucial, it can be easy to surrender to a less-than-stylish ensemble. However, this ensemble is a clear example that you can actually stay comfortable and remain equally stylish in the winter months.