For an outfit that's pared-down but can be styled in a ton of different ways, opt for a bomber jacket and a teal crew-neck t-shirt. For something more on the daring side to complement this look, complement this look with black leather high top sneakers. Can you see how extremely easy it is to look stylish and stay cozy when fall arrives, all thanks to looks like this one? A reliable option outfit proper for teen guys who prefer casual clothing outside of school.