A dark brown overcoat and navy skinny jeans are the kind of a foolproof casual look that you need when you have no time to dress up. If you need to immediately up your getup with shoes, complement this look with a pair of brown leather chelsea boots. This combination is the definition of perfect for when leaves turn yellow and red and fall is at its best. Rest assured this look is something you can totally wear as a 50-year-old guy.