If the situation calls for an effortlessly classic look, go for a navy overcoat and blue jeans. Add a pair of dark brown leather casual boots to this look and you're all done and looking boss. In the winter months, when practicality is top priority, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. However, this ensemble proves that you can actually stay toasty and remain stylish at the same time in the winter months. In this, any middle-aged man is bound to put the younger crowd to shame.