We love the way this combo of a dress shirt and white dress pants immediately makes any gentleman look stylish and sophisticated. A pair of brown oxford shoes looks perfect here. During the winter months, when warmth is key, it can be easy to settle for a less-than-stylish ensemble. This ensemble, however, is a striking illustration that you can actually stay cozy and remain equally stylish in the winter months. If you're wondering how you should dress as a 40-year-old gent, this combination gives a fair idea.