This elegant combination of a suit and a grey v-neck sweater is a popular choice among the sartorially superior chaps. Spice up this outfit with a dressier kind of shoes, like this pair of black leather oxford shoes. When leaves are falling down and temperatures are starting to drop, you'll love this outfit as your go-to for weird fall weather. Clothing like this is something a guy should definitely treat himself to as he passes the big four-oh.