Pair a tan varsity jacket with grey dress pants to assemble an effortlessly stylish and pulled together ensemble. Let your styling credentials truly shine by finishing this outfit with a pair of loafers. This one is an obvious idea if you're picking out a cool summer-to-fall ensemble. As a gent in his 30s, you want to start dressing more like a mature gentleman. That's when ensembles like this come in very handy.