You can be sure you'll look nice and stylish in a brown overcoat and white dress pants. You could take the casual route in the shoe department by slipping into desert boots. During the winter months, when practicality is paramount, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is a good illustration that you can actually stay comfortable and remain stylish at the same time in the winter months. Those wondering how to dress with style after forty, you have your answer.