Master the casual and cool look by wearing a hoodie and black skinny jeans. You can stick to a classier route when it comes to footwear by wearing black leather casual boots. In winter, when functionality is prized, it can be easy to settle for a less-than-stylish outfit in the name of functionality. This outfit, however, is a clear example that you totally can stay warm and remain equally stylish in winter. This pairing shows how guys in their thirties succeed in the fashion department.