Consider teaming a shearling coat with black jeans to feel instantly confident in yourself and look cool and relaxed. You can take a classic approach with footwear and add a pair of dark brown leather casual boots to the equation. During the winter season, when warmth is critical, it can be easy to settle for a less-than-stylish look. But this look is a clear example that you can actually stay comfy and remain stylish at the same time during the winter season. Those wondering how to dress fashionably as you pass the big five-oh, you have your answer.