A convertible carrying case having a first container and a second container that is convertible between a primary configuration and a secondary configuration. Each container having a primary face (with primary access structure for accessing the interior of the container when the convertible carrying case is in the primary configuration) and a secondary face (with secondary access structure for accessing the interior of the container when the convertible carrying case is in the secondary configuration). A first matable half and a second matable half of an openable-closeable connection are connectable to secure the containers in either a primary configuration or a secondary configuration. Preferably, contents within the containers may remain during conversion between the primary configuration and the secondary configuration. A method for converting a convertible carrying case between the primary configuration and the secondary configuration.