A shearling coat and navy skinny jeans are a smart pairing to take you throughout the day. If you want to effortlessly bump up your getup with a pair of shoes, why not add a pair of black leather casual boots to this look? During the colder months, when practicality is top priority, it can be easy to settle for a less-than-stylish look in the name of practicality. This look, however, is a clear example that you can actually stay snug and remain stylish during the colder months. Guys who wonder how to wear cool casual dressing after thirty, this ensemble should answer your question.