For an ensemble that's worthy of a modern sartorially savvy guy and casually neat, wear a waistcoat with navy jeans. You could perhaps get a little creative when it comes to footwear and introduce a pair of brown leather low top sneakers to the mix. This look isn't a hard one to nail and it's summer-ready, which is more important when it's roasting hot outside. Guys who wonder how to dress fashionably as you reach your 50s, you have your answer.