For a cool and relaxed outfit, rock a black and white shearling jacket with sweatpants — these two items fit really cool together. You know how to bring a dash of sophistication to this outfit: black chelsea boots. In the colder months, when warmth is above all, it can be easy to settle for a less-than-stylish look in the name of practicality. This look, however, is a striking illustration that you can actually stay snug and remain equally stylish in the colder months. As a 30-something Millennial gentleman, you want to start dressing more professionally. In this case, looks like this are a life saver.