Go for a straightforward but sharp option teaming an overcoat and black chinos. Does this getup feel too classic? Introduce a pair of athletic shoes to shake things up. In the colder months, when functionality is everything, it can be easy to settle for a less-than-stylish look. But this look is a striking example that you totally can stay comfortable and remain stylish at the same time in the colder months. This is a stylish yet age-appropriate combination for a 40-something man.