For something on the casually cool side, test drive this combination of a red sweatshirt and a long sleeve shirt. Hesitant about how to finish off your look? Finish off with black leather derby shoes to lift it up. In the winter months, when warmth is the priority, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look is a good illustration that you totally can stay cozy and remain stylish during the winter months.