So as you can see, it doesn't require that much effort for a man to look stylish. Marry a dark brown overcoat with a crew-neck sweater and you'll look amazing. Go off the beaten path and change up your outfit by rounding off with a pair of dark brown suede loafers. With an outfit like this in your winter arsenal, you're guaranteed to stay toasty and look awesome despite the cold temperatures. So if you need style ideas on how to dress after 50, this combo is a perfect example.