For a casual look, choose a shearling jacket and navy jeans — these two pieces fit nicely together. Elevate this look with derby shoes. In the winter season, when comfort is top priority, it can be easy to settle for a less-than-stylish look. This look, however, is a practical illustration that you totally can stay snug and remain stylish at the same time in the winter season. This pairing proves 60-year-old gentlemen can still very well kill in the style department.