Various arrangements for a flexible package for articles of footwear or other items are presented. The flexible package generally includes a lightweight flexible package sized to accommodate a pair of shoes. The flexible package may also include a removable stiffening insert to aid in maintaining the structure of the flexible package and allow stacking of the package. Further, the flexible package may include one or more handle arrangements. Various closure arrangements may be used with the flexible packaging for footwear, such as an undercut tab arrangement, hook and loop type closure arrangement, rim and lip, and the like.