This combo of a charcoal plaid overcoat and khaki print chinos might pack a punch, but it's extremely easy to pull together too. You can take a more laid-back approach with shoes and complement your look with a pair of white canvas low top sneakers. You see here this combination is also a perfect example of how to dress stylishly in the winter season. And if we're talking casual dressing ideas for gentlemen in their fifties, this outfit is perfect.