A shoe with an air circulation system, comprising: an upper having an outer layer, a porous middle layer formed of a porous material, and an inner layer, the inner layer having one or more inner layer openings for venting an inside of the upper to the middle layer, the outer layer having one or more vent openings for venting air out of the porous middle layer to outside of the upper; and a sole including an outsole, midsole, and an insole; said sole having an external air intake port, a compressible pumping chamber located in a heel area of the shoe, the external air intake port being located at a level above a level of the pumping chamber, an inlet fluid passageway connecting the external air intake port and the pumping chamber, an inlet check valve in the inlet fluid passageway between the pumping chamber and the external air intake port, a three dimensional mesh material air distribution pad located within the shoe, an outlet check valve between the pumping chamber and the air distribution pad, an outlet fluid passageway connecting the chamber and the air distribution pad, one or more peripherally and upwardly extending channels provided in the insole or midsole connecting the chamber and the porous middle layer of the upper; the pumping chamber being operable by periodic pressure applied thereto by walking in the shoe by a wearer, which causes air to be drawn into the pumping chamber from the external air intake port through the inlet fluid passageway and expelled from the chamber through the outlet fluid passageway to the air distribution pad and to one or more peripherally and upwardly extending channels provided in the insole or midsole and through the porous middle layer of the upper to the outer layer vent openings. an upper having an outer layer, a porous middle layer formed of a porous material, and an inner layer, the inner layer having one or more inner layer openings for venting an inside of the upper to the middle layer, the outer layer having one or more vent openings for venting air out of the porous middle layer to outside of the upper; and a sole including an outsole, midsole, and an insole; said sole having an external air intake port, a compressible pumping chamber located in a heel area of the shoe, the external air intake port being located at a level above a level of the pumping chamber, an inlet fluid passageway connecting the external air intake port and the pumping chamber, an inlet check valve in the inlet fluid passageway between the pumping chamber and the external air intake port, a three dimensional mesh material air distribution pad located within the shoe, an outlet check valve between the pumping chamber and the air distribution pad, an outlet fluid passageway connecting the chamber and the air distribution pad, one or more peripherally and upwardly extending channels provided in the insole or midsole connecting the chamber and the porous middle layer of the upper; the pumping chamber being operable by periodic pressure applied thereto by walking in the shoe by a wearer, which causes air to be drawn into the pumping chamber from the external air intake port through the inlet fluid passageway and expelled from the chamber through the outlet fluid passageway to the air distribution pad and to one or more peripherally and upwardly extending channels provided in the insole or midsole and through the porous middle layer of the upper to the outer layer vent openings.