Wear a long sleeve shirt with chinos to feel 100% confident in yourself and look laid-back and cool. In the winter months, when practicality is a must, it can be easy to settle for a less-than-stylish look. This look, however, is a stark illustration that you totally can stay toasty and remain equally stylish during the winter months. If you're not sure how to dress age-appropriately, this outfit is a practical illustration.