For an outfit that's worthy of a modern fashion-savvy guy and effortlessly smart, consider wearing a polo neck sweater and charcoal jeans. For something more on the classy end to complement your look, introduce a pair of dark brown leather tassel loafers to the equation. Can you see how super easy it is to look on-trend and stay warm when chillier weather hits, all thanks to getups like this one? Surely a great option if we're talking dressing ideas for adolescent guys.