Putting together a waistcoat and a white and black dress shirt will be definitive proof of your styling savvy. Finishing with a pair of brown leather chelsea boots is a surefire way to add a more laid-back aesthetic to this getup. In the winter months, when comfort is critical, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. This ensemble, however, is a shining example that you totally can stay snug and remain equally stylish in the winter months. This ensemble suggests how to look good as you age into your 40s.