For classy style with a clear fashion twist, go for a black overcoat and a grey three piece suit. Brown leather casual boots will add an easy-going feel to an otherwise traditional look. During the winter months, when comfort is a must, it can be easy to settle for a less-than-stylish look in the name of practicality. However, this look is a striking example that you can actually stay comfy and remain stylish in the winter months. This combination proves 50-something gents can still very well turn heads.