For an outfit that's city-style-worthy and casually classic, make a grey double breasted blazer and a long sleeve shirt your outfit choice. And if you wish to instantly step up your outfit with a pair of shoes, add olive suede tassel loafers to the mix. This outfit is an appealing pick if you're on the hunt for a knockout look that will take you from summer to fall. So if you're hunting for style tips on how to dress as you age into your 50s, this outfit is definitely worth saving for later.