Pairing a crew-neck sweater with black chinos is a safe and very fashionable bet. A pair of dark brown leather desert boots can integrate seamlessly within a multitude of outfits. In the winter season, when warmth is prized, it can be easy to surrender to a less-than-stylish getup in the name of practicality. But this getup is a shining example that you totally can stay toasty and remain equally stylish during the winter season. And if we're talking style for teen guys, this look looks good on most.