In general, the present invention is directed to a reusable two-way mailing bag that may include a pouch configured to receive a shipping or postage label; an internal cavity, the internal cavity further comprising a pocket; and a closing device for closing the internal cavity; configured to be folded into the pocket such that the pouch may be visible. In accordance with some embodiments, a reusable two-way mailing bag may include a double-sided pouch configured to receive a shipping or postage label; an internal cavity comprising a pocket; a zipper for providing access to and closing the internal cavity; and an attachment device; the two-way mailing bag foldable into the pocket such that the double sided pouch is visible when the two-way mailing bag is an folded or unfolded position, and the attachment device engagable to maintain the two-way mailing bag folded into the pocket.