For an ensemble that's city-style-worthy and effortlessly neat, dress in a charcoal overcoat and grey chinos. To give your overall outfit a more relaxed spin, complete this outfit with a pair of grey athletic shoes. A kick-ass look that will take you from summer to fall like this one makes it very easy to welcome the new season. This outfit illustrates that as a gentleman over 50, you still have a wide range of styling options.