A blazer and a charcoal dress shirt are a truly smart look to try. Black suede loafers look awesome finishing off this ensemble. During winter, when functionality is key, it can be easy to settle for a less-than-stylish ensemble. This ensemble, however, is a shining example that you totally can stay comfortable and remain equally stylish during winter. Wondering how you should dress as you age into your 40s? This combination is the perfect answer.