Wear a grey vertical striped double breasted blazer and grey vertical striped dress pants for seriously stylish style. Grab a pair of black leather derby shoes and the whole ensemble will come together perfectly. During the winter season, when warmth is key, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. This ensemble, however, proves that you totally can stay cozy and remain stylish during the winter season.