Understanding that clothing has a serious place in a man’s life doesn’t mean his clothing always has to be serious. Having an appropriate tongue-in-cheek humor in what you wear is good for both contrast game and also conveys amused mastery. It says, “I know what my clothing says about me and I only care as much as I need to.” It can be intriguing.

The key is to have some subtle fun. If you break all the rules it will look like you don’t know them. But following everything and breaking a single sartorial or conventional standard can show you don’t care too much. The sharks eating the fish on this tie are great. From far away you won’t notice, but up close it gets the right kind of attention.