The invention is an inflatable inner sole for footwear which has a flexible, inflatable enclosure with an inflation system that preferably includes an on-board air pump and a pressure relief valve. In this invention the inner sole has a sheet and/or foam cover or surround on the flexible enclosure for enhanced comfort. Useful sheet covers can be plastic, including rubber, films in solid or foamed state, or fabric which are applied against the upper, wearing surface of the inflatable enclosures. The covers can be bonded only to the edges of the inflatable enclosures to permit relative movement between the covers and enclosures, or can be bonded to the top surface of the enclosures, or formed as surrounds which encapsulate the inflatable enclosures.