Teaming a black double breasted blazer and white chinos is a surefire way to inject your styling routine with some masculine sophistication. Introduce a pair of black leather double monks to the equation for an instant style upgrade. During the winter months, when warmth is critical, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is a bright example that you totally can stay comfortable and remain stylish in the winter months. Wondering how to dress your age as you age into your 50s? This pairing is a wonderful example.