For a look that provides functionality and dapperness, dress in a shearling jacket and grey ripped skinny jeans. You can take a classic approach with shoes and throw in a pair of casual boots. In the winter season, when comfort is a must, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. But this ensemble is a vivid example that you can actually stay comfy and remain equally stylish during the winter season.