One of the coolest ways to style out a crew-neck sweater is to wear it with black leather skinny pants. You could perhaps get a bit experimental on the shoe front and elevate this ensemble by slipping into black pumps. During the winter season, when functionality is the priority, it can be easy to surrender to a less-than-stylish look in the name of practicality. But this look is a good illustration that you can actually stay comfortable and remain equally stylish in the winter season.