Go for something stylish and timeless in a brown houndstooth overcoat and blue wool dress pants. Our favorite of a multitude of ways to finish off this getup is a pair of dark brown suede chelsea boots. During the winter months, when warmth is a must, it can be easy to settle for a less-than-stylish outfit in the name of convenience. This outfit, however, is a practical illustration that you totally can stay comfortable and remain equally stylish in the winter months. Timeless combinations like this are worth having in your wardrobe no matter how old you are.