When it comes to timeless smart style, this pairing of a tan shirt jacket and grey chinos doesn't disappoint. To give this outfit a more laid-back twist, add dark brown leather low top sneakers to the equation. As you can see, it's super easy to look dapper and stay toasty when chillier weather hits, thanks to this ensemble. If you frequently wonder how to dress appropriately for your age without giving up on fashion, this pairing is a life saver.