A combination carrying device includes a rigid basket having a flexible bag nested therein. The flexible bag may be formed from one or more fabrics or like materials and define a tapered volume having a pair of handle extensions. The rigid basket may be formed from plastics or like materials and include rotatable handles disposed on an upper perimeter thereof, and may also define a tapered volume which corresponds to the tapered volume of the flexible bags. A customer carrying a combination carrying device in a materials handling facility (e.g., a warehouse or retail establishment) may place one or more items in the flexible bag nested within the rigid basket, and extract the flexible bag from the rigid basket upon arriving at a destination or after executing a purchase for the items therein.