For an outfit that's super simple but can be dressed up or down in many different ways, marry a light blue dress shirt with navy chinos. Black leather derby shoes are a fail-safe way to give a dose of sophistication to your outfit. Many people suppose that just because it is snowing outside you have to sacrifice smart style, but that's just not true, and this outfit is a clear example. So as you can see this outfit is something you can totally wear as a gent over 50.