If you feel more confident in comfortable clothes, you'll love this off-duty pairing of a red crew-neck sweater and chinos. Finishing with a pair of white leather low top sneakers is a fail-safe way to introduce a carefree vibe to your ensemble. And if you're looking for a cool look that will take you from winter to spring, this one is great. Relaxed combos for teenage boys aren't actually that hard, as you can see.