Team a dark green wool turtleneck with grey chinos to effortlessly deal with whatever this day throws at you. For something more on the classier end to complete your getup, introduce a pair of dark brown leather casual boots to the mix. A knockout getup that will take you from summer to fall like this one makes it very easy to welcome the new season. Wondering what you should wear as you age into your 50s? This outfit is a practical example.