For an outfit that's very simple but can be manipulated in a ton of different ways, wear a navy denim shirt and a v-neck t-shirt. Avoid looking too casual by finishing with a pair of dark brown leather brogues. During the winter months, when practicality is paramount, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. But this ensemble is a vivid example that you totally can stay warm and remain equally stylish in the winter months.