Opt for a navy overcoat and khaki chinos to create an effortlessly neat and well-executed outfit. If not sure as to what to wear in the shoe department, add a pair of casual boots to the mix. During the colder months, when comfort is top priority, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. This ensemble, however, is a clear example that you can actually stay cozy and remain stylish at the same time during the colder months. A fail-safe option combo proper for middle-aged men.