When it comes to high-octane dapper style, this combo of a charcoal overcoat and grey wool dress pants doesn't disappoint. Introduce a pair of dark brown leather loafers to this getup to make a classic outfit feel suddenly edgier. With an outfit like this in your winter arsenal, you're guaranteed to stay toasty and look awesome despite the nasty weather. This pairing demonstrates that even after 50 you still have a wide array of styling options.