The wearables field has been linked to speculative ideas, sci-fi books and films, and other imaginary media for decades. Most superheroes and villains are equipped with a magical gadget, cape, or shoes that enhance their superpowers. Sometimes the magic is embedded in the wearable, leaving us to believe that anyone with a particular hat or cloak could be transformed into a wizard. Other times the wearable simply enhances these powers, making them seem more far-fetched for everyday use. This chapter traces the evolution of fictitious wearables, connecting them to inventions and ideas that actually exist today.