A wearing simulation device includes a first animation generation unit that generates a first animation indicating a change in a movement of a body and a surface shape of the body from a second posture to a first posture, a second animation generation unit that generates a second animation indicating a change in a movement of the body and a surface shape of the body in a continuous movement, a third animation generation unit that generates a third animation by connecting the first animation and the second animation, and a simulation execution unit that makes the body wear a clothing model in at least one frame from beginning of the third animation, deforms the clothing model so as to follow the change in the movement of the body and the surface shape of the body in the frame after wearing, and simulates a shape change of the clothing model.