Marrying a light blue blazer and a dress shirt will be a true demonstration of your sartorial prowess. Rounding off with a pair of navy suede tassel loafers is a surefire way to inject a dash of elegance into this outfit. Seeing as temperatures are dropping, this look seems a viable option for the time in between seasons. This outfit illustrates that figuring out fashion as you head into your 50s is totally doable.