This laid-back combination of a light blue vertical striped shirt jacket and grey chinos is perfect if you want to feel confident in your outfit. Complete your getup with white athletic shoes to infuse a dose of stylish nonchalance into this getup. This is a surefire option for a kick-ass outfit that transitions easily into spring. Relaxed casual getups for stylish guys over 40 aren't actually that hard, as you can see here.