For a look that's polished and GQ-worthy, go for a navy wool waistcoat and grey wool dress pants. If you want to effortlessly dial down this outfit with a pair of shoes, add a pair of navy suede chelsea boots to the equation. Seeing as fall is in full swing, this look seems a viable choice for in between seasons. A vivid example for any gentleman who's still working out how to dress at 40 plus.