For a look that's nothing less than envy-worthy, consider pairing an olive blazer with a dress shirt. Bring a more relaxed twist to by slipping into dark brown leather casual boots. In winter, when practicality is imperative, it can be easy to surrender to a less-than-stylish outfit in the name of practicality. This outfit, however, is a good illustration that you can actually stay toasty and remain equally stylish in winter. Those who wonder how to stay stylish in your forties, you have your answer.