Consider wearing a crew-neck sweater and black skinny jeans for comfort dressing with a twist. For something more on the relaxed end to finish off this outfit, introduce dark brown lace-up flat boots to the mix. In the winter months, when functionality is paramount, it can be easy to surrender to a less-than-stylish look. This look, however, is a stark illustration that you can actually stay warm and remain seriously stylish at the same time in the winter months.