A convertible earcup for a headphone. The earcup includes an earcup frame, a driver positioned within the earcup frame and an earpad coupled to the earcup frame. The earpad is operable to be converted between a first configuration in which the earpad comprises a first diameter and a second configuration in which the earpad comprises a second, different diameter. A convertible headphone system including a set of earcups. Each earcup within the set of earcups includes a speaker unit and an earpad, and the earpad is convertible between a first diameter and a second diameter.