This combination of a beige turtleneck and brown dress pants is a surefire option when you need to look classy and incredibly sharp. If you're wondering how to finish off, add double monks to this getup. So as you can see, this look is sharp and will provide the necessary warmth for getting through the winter season with ease. This outfit illustrates that dressing stylishly as a man over 50 is not that daunting a task.