Putting together an overcoat and a black blazer is a fail-safe way to infuse your styling arsenal with some manly refinement. On the shoe front, go for something on the relaxed end of the spectrum and complement your outfit with black leather casual boots. It's easy to see how this getup will keep you snug and stylish all winter long. This combination proves that staying fashionable as a 40-year-old man is quite manageable.