This pairing of a black crew-neck sweater and charcoal dress pants is a real lifesaver when you need to look effortlessly sleek in a flash. If not sure about the footwear, stick to a pair of brown leather chelsea boots. In the colder months, when functionality is critical, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. This ensemble, however, is a good illustration that you totally can stay comfortable and remain equally stylish in the colder months.