Holly was seen as sacred to the European druids and the Romans considered it the plant of Saturn. As the Christian faith began to spread throughout Europe, holly quickly became a symbol of Christmas. Henry VIII, a known writer of songs (see Greensleeves), wrote a love song featuring the plant.
The carol "The Holly and the Ivy" may possibly be older than an early 18th century mention of it in a broadside. However, there are manuscripts explaining ancient English villages holding singing contests during the winter solstice, where the men sang about holly (seen as masculine) and the women sang about ivy (seen as feminine). Of course the only resolution to this contest was underneath the mistletoe. These three plants are prominent in England during the winter.