If it's comfort and practicality that you appreciate in menswear, marry a long sleeve shirt with light blue jeans. You can take a classic approach with shoes and add a pair of brown casual boots to the mix. So as you can see, it's a stylish, not to mention season-appropriate, ensemble to keep in your transeasonal rotation. As you're maturing from a kid to a teenage boy, you probably want to look older. If that's the case, looks like this are perfect as inspiration.