A white turtleneck and blue jeans are a savvy combo that will effortlessly carry you throughout the day. Does this outfit feel too dressy? Introduce olive athletic shoes to shake things up. In the winter months, when comfort is everything, it can be easy to settle for a less-than-stylish outfit in the name of functionality. But this outfit is a striking example that you totally can stay comfy and remain equally stylish in the winter months. Casual getups for stylish gentlemen over 50 aren't actually that hard, as you can see here.