Reach for a charcoal vertical striped suit and a white dress shirt for a classic and classy silhouette. Complete your ensemble with black leather derby shoes et voila, the look is complete. During the winter months, when comfort is crucial, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. But this ensemble is a good illustration that you totally can stay toasty and remain stylish at the same time during the winter months. Getups like this have a sophisticated air that suit 50-something men very well.