A charcoal vertical striped suit and a white dress shirt are a really sharp combo to try. Our favorite of a multitude of ways to finish off this outfit is with black leather derby shoes. In the colder months, when practicality is key, it can be easy to surrender to a less-than-stylish ensemble. However, this ensemble is a clear example that you totally can stay snug and remain equally stylish in the colder months. If you're often not sure how to dress appropriately for your age without giving up on fashion, this outfit is a never-failing option.