So as you can see, it doesn't require that much effort for a man to look effortlessly sophisticated. Just consider wearing a navy overcoat and a brown wool turtleneck and be sure you'll look incredibly stylish. Want to play it up when it comes to footwear? Complement this outfit with olive velvet loafers. A great example of transitional fashion, this outfit is ideal when spring comes. This is a practical example of how to dress with style as you pass the big 5-0.