A portable cooler assembly includes sidewalls connected by a bottom wall. The sidewalls and bottom wall collectively define an interior space. A rim is attached to a top of the collapsible side walls, and a lid is supported on the rim and encloses the interior space. A base defines a container receiving recess within which the bottom wall is received and supported. A drain conduit defines a passageway in fluid communication with a lower portion of the interior space. When the portable cooler assembly is in a first configuration, the collapsible sidewalls extend outwardly from the container receiving recess. When the portable cooler assembly is in a second configuration, the collapsible sidewalls are completely received within the container receiving recess in a collapsed condition, and an outer peripheral edge portion of the rim is at least partially received within the container receiving recess.