A cooler assembly for the storage of one or more objects includes a cooler portion having a main portion and a cover portion that is removably or pivotable relative to the main portion. First and second main portion securement features are disposed on a side wall of the main portion, and the first and second main portion securement features may be identical. First and second attachment assemblies, which may include a container, have identical first and second attachment securement features, respectively, which may releaseably engage either of the first and second main portion securement features to allow the first and second attachment assemblies to be transported with and stored on the cooler portion.