A portable cooler assembly comprises a base and an insulated container defining a cooler. The container includes an inflatable wall and a valve for inflating of the wall. The insulated container is removably coupled to the base, and the base defines a container receiving recess within which a bottom portion of the insulated container is received. When the portable cooler assembly is in a first configuration, the inflatable wall is inflated and extends outwardly from the container receiving space. When the portable cooler assembly is in a second configuration, the inflatable wall is deflated and is completely received within the container receiving space in a collapsed condition.