A collapsible shipping bag includes a body defining an interior, the body including a top wall, a bottom wall, a right sidewall, and a left sidewall. The collapsible shipping bag further includes a plurality of inner stiffener panels disposed within the interior and dividing the interior into a plurality of pockets, each of the plurality of inner stiffener panels defining an intersection with the top wall and the bottom wall. The collapsible shipping bag further includes a strap coupled to the body at a first plurality of intersections with the top wall and uncoupled from the body at a second plurality of intersections with the top wall. The body is movable from an expanded position to a collapsed position due to movement of the straps.