As you can see, it doesn't require that much effort for a man to look casually classic. Make a grey suit and a dark brown raincoat your outfit choice and you'll look incredibly stylish. Introduce tassel loafers to the mix to take things up a notch. You can bet this getup will become your uniform when colder weather arrives. Those who wonder how to stay stylish as you move into your 50s, you have your answer.