A cooler includes a base; an upper rim; and a collapsible wall extending between the base and the upper rim. The cooler wall is capable of transitioning between a fully collapsed configuration and a fully expanded configuration and is stable in each configuration. Additionally, in transitioning between the fully collapsed and fully expanded configurations, the cooler transitions to at least one intermediate configuration in which the cooler is in a stable state and may be used. The collapsible wall preferably comprises a flexible membrane that is configured to be collapsible between three or more stable states, and preferably is formed from silicone.