This combo of a black floral short sleeve shirt and khaki chinos makes for the ultimate off-duty style for any gentleman. Throw white and navy leather high top sneakers in the mix to make a mostly dressed-up getup feel suddenly edgier. So as you can see, it's super easy to look awesome and stay snug come cooler weather, thanks to this outfit. Wondering how to nail casual dressing as you move into your 40s? This combination is a vivid example.