Team a tan crew-neck sweater with blue chinos for a casual getup with a twist. Go the extra mile and jazz up your look by slipping into brown suede casual boots. In the winter season, when functionality is crucial, it can be easy to settle for a less-than-stylish outfit. This outfit, however, is hard proof that you totally can stay cozy and remain equally stylish during the winter season. If you're wondering how you should dress as a teenage boy, this ensemble is a good source of inspiration.