For classy style with a modern spin, pair a grey overcoat with a charcoal wool suit. And if you need to instantly tone down this look with footwear, why not introduce dark brown leather loafers to the mix? During the winter months, when comfort is top priority, it can be easy to settle for a less-than-stylish ensemble. But this ensemble is a shining example that you totally can stay warm and remain equally stylish in the winter months. Wondering how to dress your age well into your 40s? This combo is the perfect answer.