A button assembly including a button head operable to rotate in three-dimensional space. The button assembly having a mounting portion and an elongated shaft attached to a base is provided. The button assembly includes a bearing member disposed on one end of the shaft. The bearing member is configured to fittingly engage the mounting portion of the button head so as to pivotably attach the button head to the shaft. The base may be inserted into an article of clothing in alignment with a corresponding buttonhole. Accordingly the user is able to rotate and pivot the button head about the bearing member of the shaft so as to facilitate the insertion of the button head into the buttonhole.