A shoe having an upper, a sole and an adjustable heel assembly including a first heel member connected to the sole at a rear portion thereof and a second heel member arranged at least partially within the first heel member. The second heel member is movable relative to the first member between a first position in which the first and second heel members provide the heel with a first height and a second position in which the first and second heel members provide the heel with a second height greater than the first height. An improved self stabilizing second heel member with a beveled bottom surface is provided which has a first contact surface contacting the ground in the first position and a second contact surface contacting the ground in the second position.