For an ensemble that's super straightforward but can be manipulated in a multitude of different ways, marry a long sleeve t-shirt with blue jeans. Amp up the formality of your look a bit by finishing with a pair of black leather chelsea boots. This one is a viable choice when it comes to figuring out a cool getup for awkward transition weather. As you're transitioning from a kid to a teen boy, you probably want to look older. In this case, combinations like this are a goofproof option.