A self-ventilating shoe assembly including an upper having an outer layer, a porous middle layer, and an inner layer; and a sole including an outsole; is provided with one or more passageways or chambers connecting between the outsole and the porous middle layer of the upper. One or more external vent openings are in fluid communication with the one or more passageways or chambers. Cooling ambient air is moved by convection and by a pumping action from the external vent openings through the passageways or chambers up through the porous middle layer of the upper, and optionally, the insole, providing cooling and reducing moisture in the cavity containing the wearer's foot.