One of the most elegant ways to style such a timeless menswear item as a grey vertical striped suit is to team it with a white dress shirt. As for shoes, introduce black leather dress boots to the equation. During the winter months, when functionality is essential, it can be easy to settle for a less-than-stylish getup. However, this getup is a striking example that you totally can stay toasty and remain equally stylish during the winter months. The ability to sport combinations like this is one of the perks of middle age.