Opt for a tan trenchcoat and grey chinos and you'll be the picture of manly sophistication. Tobacco suede tassel loafers will take your look a classier path. When you're having one of those gloomy autumn days, sometimes only a cool outfit like this one can get you out the door in the morning. So as you can see, as an over-50 guy, you still have a wide range of dressing options.