For an outfit that's super simple but can be smartened up or dressed down in many different ways, wear a navy shirt jacket and blue chinos. Our favorite of a great number of ways to complete this look is brown leather tassel loafers. This combination is a smart pick if you're picking out a well-coordinated outfit for transeasonal weather. This pairing illustrates that dressing cool as you age into your 50s is easier than one might think.