For a casual look, reach for a black blazer and black skinny jeans — these two items play perfectly together. If you wish to effortlessly perk up this ensemble with a pair of shoes, why not complete your ensemble with a pair of derby shoes? Undoubtedly, it's easier to work through a boiling hot afternoon in a summery combo such as this one. As you're transitioning from a kid to an adolescent boy, you probably want to start dressing more like an adult. That's when looks like this are a winning option.