To achieve a laid-back outfit with a modern twist, try teaming a black shearling jacket with cargo pants. If you don't know how to finish, a pair of dark brown desert boots is a wonderful option. In the winter season, when warmth is essential, it can be easy to surrender to a less-than-stylish getup. But this getup is a stark illustration that you can actually stay comfortable and remain equally stylish in the winter season. As you see here, even after 50 your sartorial options are still pretty much limitless.