A tan waistcoat and multi colored shorts are absolute staples if you're figuring out a sharp closet that matches up to the highest sartorial standards. Feeling creative? Change up this outfit by sporting a pair of dark brown leather derby shoes. This outfit isn't a hard one to score and it's summer-appropriate, which is most important when it's extremely hot outside. Gents wondering how to sport smart outfits as you drift through your 20s, you have your answer.