This laid-back pairing of a black shearling jacket and black ripped skinny jeans is very easy to put together in no time, helping you look dapper and ready for anything without spending too much time digging through your closet. Here's how to dress up this getup: black leather chelsea boots. During winter, when warmth is imperative, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. But this ensemble is hard proof that you totally can stay cozy and remain equally stylish during winter. A nice, less conservative ensemble for a 20-year-old man.