An expandable and collapsible cooler includes: a base defining a bottom portion of the cooler; an upper rim defining an upper portion of the cooler; a collapsible cooler wall extending between and attached to said base and said upper rim and surrounding an interior storage space of the cooler, the cooler wall comprising a flexible elastomeric membrane that includes a plurality of hinge lines at which the membrane is configured to bend such that the membrane is transitional between a collapsed configuration and an expanded configuration; and a drain conduit comprising a passageway providing fluid communication between an exterior of the cooler and the interior storage space or the intermediate space. The cooler is transitional between an expanded configuration for use of the cooler, and a collapsed configuration during nonuse of the cooler, by bending along the hinge lines, each configuration corresponding to a stable configuration of the cooler.