So as you can see, it doesn't take that much time for a man to look effortlessly smart. Wear a tobacco puffer jacket with grey plaid chinos and you'll look incredibly stylish. And if you need to immediately perk up this outfit with a pair of shoes, introduce black leather tassel loafers to the mix. This getup is a pretty wonderful choice, especially for autumn, when the temperature is dipping. This is a perfect example of how to stay stylish well into your 50s.