Why not dress in a white and navy long sleeve t-shirt and jeans? Both of these items are totally functional and will look awesome when worn together. Our favorite of a countless number of ways to complete this look is a pair of burgundy leather oxford shoes. Crafting a well-coordinated look can be a bit challenging on its own. Add extra cold temperatures into the equation, and the whole thing becomes even more difficult. Don't despair, this here is your winter outfit inspiration. This ensemble proves that figuring out how to dress well as a gentleman over 50 is not that hard.