A dress shirt and a charcoal overcoat are essential in a functional man's closet. When it comes to footwear, this ensemble is rounded off really well with chelsea boots. In the winter months, when warmth is prized, it can be easy to surrender to a less-than-stylish getup in the name of convenience. However, this getup is a stark illustration that you can actually stay cozy and remain equally stylish in the winter months. Clothing like this is something a gent should definitely treat himself to as he steps into his 60s.