For something more on the relaxed side, you can easily dress in a shirt jacket and grey sweatpants. Dark brown tassel loafers are a guaranteed way to bring an added dose of style to this ensemble. So if you're after an easy-to-transition outfit, look no further. As you're transitioning from a kid to a teenage boy, you probably want to start dressing more like an adult. That's when combinations like this come in very useful.