Earbud headphones may be configured to be secured to a user's outer ear. The earbud headphones may comprise a speaker assembly configured to convert an audio signal into a sound wave audible to the human ear. A main body portion may support the speaker assembly. An extension may extend from the main body portion away from the speaker assembly to define a gap between the extension and the speaker assembly. The gap may be sized and positioned to receive a portion of a user's outer ear within the gap such that the portion of the user's outer ear is disposed between the extension and the speaker assembly and retains the earbud headphone in the ear of the user when the earbud headphone is worn by the user.