For a goofproof casual option, you can never go wrong with this combo of a long sleeve shirt and tobacco chinos. Introduce black leather loafers to this ensemble for a masculine aesthetic. Undoubtedly, an outfit like this will keep you warm and stylish, rain or shine. And if we're talking dressing ideas for teen boys, this getup looks nice on most.
Consider teaming a long sleeve shirt with tobacco chinos for a comfortable outfit that's also pulled together. A pair of black leather casual boots instantly classes up any outfit. This combination is a really nice pick, especially for autumn, when the temperatures are getting lower. This getup is most probably exactly what you're looking for as a teenager.