Extremely chic, this combination of a charcoal blazer and navy check dress pants will provide you with variety. When it comes to footwear, this look pairs nicely with black leather ankle boots. During the colder months, when practicality is the priority, it can be easy to surrender to a less-than-stylish look. This look, however, is hard proof that you can actually stay warm and remain totaly chic during the colder months.