A shoe with a detachable heel includes: a heel post; a heel cladding including an aperture shaped to receive the heel post; and an attachment mechanism secured to the heel cladding, the attachment mechanism including seated within the heel cladding wherein the attachment mechanism includes a button biased towards first position in which the attachment mechanism secures the heel post within the heel cladding and when a force is applied to overcome the bias towards the first position the button translates approximately perpendicular to the heel post to place the attachment mechanism in a second position wherein the heel post is released from within the heel cladding.