Set in feudal times, the story begins in the Kingdom of Didd, when King Derwin is riding through a street past peasant protagonist Bartholomew Cubbins. Ordered to remove his hat, according to the laws, Bartholomew does so; but another hat mysteriously appears; when he attempts to remove this one, another one appears again, and this continues as he removes more and more hats, each growing in extravagance and beauty from the 451st hat onwards. Ultimately the 500th hat, studded with massive gems and gilding, leaves Bartholomew's head bare. Stunned by the beauty of the hat, King Derwin grants him reprieve and trades him 500 gold coins for the 500th hat.