We investigated how the shape of socks influences the wearing comfort of casual socks. The adjectives used for sensory evaluation of wearing comfort were examined by the technique of the information theory. In the case of socks having different top lengths, the wearing comfort was evaluated by “easy to wear”, “stretch” and “good fit”, and the transmitted informations of the adjectives “pressure” and “stretch at the calf” are more than the other adjectives of the wearing comfort of socks. In the case of socks having different leg lengths, the wearing comfort was evaluated “stretch” and “pressure at the top”, and the transmitted informations of the adjectives “stretch at the calf” and “slipping down from the top” are more than the other adjectives.