This combo of a grey wool blazer and grey wool chinos will prove your expertise in men's fashion. You can get a little creative on the shoe front and dress up this ensemble by finishing with a pair of black leather chelsea boots. During the winter months, when warmth is critical, it can be easy to settle for a less-than-stylish look in the name of practicality. But this look is a shining example that you can actually stay warm and remain equally stylish during the winter months.