Effortlessly blurring the line between dapper and casual, this combo of a denim jacket and a crew-neck t-shirt is bound to become one of your favorites. For something more on the smart side to round off this look, complement this look with black leather derby shoes. So if it's a boiling hot hot weather day and you want to look on-trend without putting in too much work, this outfit will do the job in no time. As you're transitioning from a kid to an adolescent boy, you probably want to start dressing more like a grown-up. That's when getups like this come in handy.