For a look that's elegant and gasp-worthy, reach for a charcoal overcoat and charcoal plaid wool dress pants. If not sure about what to wear when it comes to footwear, add dark brown leather loafers to the mix. During winter, when comfort is essential, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a good illustration that you can actually stay cozy and remain equally stylish in winter.