A two-way reusable shipping container has a plurality of flexible walls, the walls surrounding an internal cavity when the shipping container is in an open state. A pouch is located on a first wall of the plurality of flexible walls, and is configured to form a pocket into which the walls of the shipping container are collapsed when the shipping container is in a compact state. A closure device is configured to retain the shipping container in the pocket in the compact state. In some embodiments, the shipping container includes inflatable pillows, each pillow being secured to one of the walls. In some embodiments, the pouch inverts when the shipping container is converted between the open and compact states, such that interior surfaces of the pocket when the shipping container is in the open state become exterior surfaces of the pocket when the shipping container is in the compact state.