Consider wearing a black leather biker jacket and charcoal dress pants if you wish to look seriously stylish without making too much effort. If you wish to effortlessly smarten up your ensemble with a pair of shoes, complete your look with navy leather derby shoes. There's nothing like a killer getup to spice up a gloomy fall afternoon. Wondering how to dress your age as you pass the big 5-0? This pairing is a good illustration.