Team a navy print sweatshirt with olive chinos to feel 100% confident in yourself and look fashionable. Finishing with a pair of red canvas high top sneakers is a surefire way to infuse a more relaxed finish into your getup. This one is a wonderful pick when it comes to picking out a well-coordinated outfit for in-between weather. Guys who are curious how to dress well as a teenage boy, here's your inspiration.