As you can see, looking casually refined doesn't require that much effort. Just opt for a white and navy vertical striped short sleeve shirt and khaki dress pants and be sure you'll look awesome. Round off with a pair of high top sneakers to effortlessly dial up the fashion factor of your getup. Clearly, it's easier to work through an extremely hot summer afternoon in a breezy ensemble like this. This outfit proves that figuring out fashion at 40 plus is not that daunting a task.