Dress in a tan crew-neck t-shirt and khaki chinos for a stylish, casual look. And if you want to easily amp up your look with one single piece, complete this ensemble with tassel loafers. This look isn't a hard one to nail and it's summer-friendly, which is important when it's roasting hot outside. If you're wondering how you should dress as a man in his fifties, this outfit gives a fair idea.