For an outfit that's super easy but can be smartened up or dressed down in a ton of different ways, wear a blazer with chinos. Balance out this getup with a classier kind of footwear, such as these black leather chelsea boots. In the winter months, when practicality is a must, it can be easy to surrender to a less-than-stylish outfit in the name of practicality. However, this outfit proves that you can actually stay comfy and remain equally stylish during the winter months. Gentlemen wondering how to wear classic and casual looks as you progress through your teens, this pairing should answer your question.