If you prefer a more casual approach to style, why not go for a grey blazer and a crew-neck t-shirt? For something more on the smart side to finish your outfit, choose a pair of black leather chelsea boots. In the winter season, when warmth is a must, it can be easy to settle for a less-than-stylish outfit. This outfit, however, is a stark illustration that you can actually stay snug and remain equally stylish in the winter season. As you're transitioning from a kid to a teen boy, you probably want to look older. If that's the case, combos like this are a lifesaver.