A white and brown dress shirt and jeans are absolute staples if you're figuring out a classy closet that holds to the highest sartorial standards. Introduce a pair of brown leather chelsea boots to the equation for a dash of class. During the colder months, when warmth is key, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look is a practical illustration that you can actually stay cozy and remain equally stylish during the colder months. This outfit demonstrates that cracking the fashion code as an over-40 gentleman is not that hard.