For comfort dressing with an urban finish, you can easily wear a white and red crew-neck t-shirt and grey sweatpants. And if you want to effortlessly step up your ensemble with a pair of shoes, throw in a pair of boat shoes. This combination is a good pick when it comes to piecing together a cool ensemble for transeasonal weather. So if you're after outfit inspiration for dressing as a teenage boy, this combination is a good example.