Go all out in a suit and a brown waistcoat. A pair of brown leather derby shoes can instantly dress down a dressy ensemble. In the colder months, when comfort is imperative, it can be easy to settle for a less-than-stylish outfit in the name of convenience. But this outfit is a shining example that you can actually stay comfortable and remain equally stylish in the colder months. This is a modern and age-appropriate ensemble for guys over 40.