During play, a toy is rotated in a horizontal circular path about a player's ankle. The toy includes a collar and a housing connected to the collar by a tether. During play, the housing rotates about the player's ankle, while the player simultaneously hops or skips the tether. The housing contains a ribbon that is extendable from the housing to any one of a selected number of lengths. The length of the ribbon extended from the housing is directly proportional to a difficulty level of playing with the skipping toy in the manner described above. That is, the longer the ribbon, the faster a player must rotate the toy to avoid contact between the ribbon and a ground or playing surface. The ribbon may be automatically or manually retracted when the player wishes to do so.