Go for a simple yet cool and casual look by marrying a black and white short sleeve shirt and jeans. You know how to dress it up: black chunky leather derby shoes. A vivid example for any man who wonders how to dress age-appropriately while still looking stylish.
A sharp combo of a black and white short sleeve shirt and jeans will bring confidence and make you feel good. And if you wish to easily amp up this getup with a pair of shoes, why not introduce brown leather casual boots to the equation? This is a pairing you, as a middle-aged gent, can always count on.