For an ensemble that's street-style-worthy and casually sleek, dress in a navy turtleneck and a navy overcoat. Chelsea boots will bring a dose of refinement to an otherwise mostly dressed-down getup. So as you can see, it's extremely easy to look awesome and stay cozy come colder weather, thanks to this getup. This getup proves that reaching age 50 is no reason for your dressing standards to drop.