Opt for a black suit and a charcoal waistcoat if you're going for a neat, fashionable ensemble. To bring a laid-back feel to this outfit, throw a pair of grey athletic shoes in the mix. If it's one of those gloomy fall afternoons, what better to cheer it up than a dapper outfit like this one? This getup is a practical illustration men in their forties can very well slay in the style department.