If you're on the lookout for a relaxed casual and at the same time seriously stylish outfit, pair a shirt jacket with a grey long sleeve t-shirt. And if you wish to effortlessly dress down your outfit with one piece, introduce a pair of navy athletic shoes to the equation. This one is a smart idea when it comes to figuring out a kick-ass outfit for transitional weather. Those who wonder whether you can still rock cool casual dressing as you slip into your 40s, you have your answer.