This combo of a black shearling jacket and grey jeans is a safe go-to for an incredibly dapper ensemble. Finish with a pair of casual boots to punch up your look. In the winter months, when warmth is paramount, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is hard proof that you can actually stay cozy and remain stylish during the winter months. If you're not sure how to dress as a younger guy, this outfit is a wonderful example.