For something on the cool and casual side, you can dress in a crew-neck sweater and wide leg pants. Now all you need is a great pair of black leather knee high boots to complete your look. In the winter season, when warmth is imperative, it can be easy to settle for a less-than-stylish look in the name of practicality. This look, however, is a practical illustration that you can actually stay snug and remain incredibly stylish in the winter season.