This refined combo of a blue overcoat and a navy vertical striped wool suit is a must-try outfit for any guy. When not sure about what to wear in the shoe department, introduce derby shoes to this look. In the colder months, when comfort is crucial, it can be easy to settle for a less-than-stylish look. This look, however, is a shining example that you totally can stay snug and remain stylish at the same time during the colder months. No doubt, a foolproof choice when it comes to fashion at 50 plus.