We love the way this pairing of a navy vertical striped wool suit and a white dress shirt instantly makes any man look polished and sharp. When not sure as to what to wear when it comes to footwear, stick to a pair of dark brown leather double monks. You can see here this combo is also a vivid example of how to dress stylishly in the dead of winter. If you want to project maturity, a look like this is a solid bet.