Consider teaming an overcoat with black chinos to look seriously sharp anywhere anytime. A pair of silver athletic shoes immediately kicks up the fashion factor of this look. During the colder months, when comfort is key, it can be easy to settle for a less-than-stylish look in the name of practicality. This look, however, is a practical illustration that you totally can stay comfortable and remain equally stylish during the colder months. Gentlemen wondering how to dress with style in your 40s, you have your answer.