Stein commissioned Picasso to paint her portrait in 1905, and the process became unusually long. She reportedly sat for him around 80–90 times. Picasso eventually became dissatisfied with the face, wiped it out, and left for Spain. When he returned, he completed the face largely from memory, giving it the angular, mask-like quality seen in the finished painting.
The portrait also captures an important moment in Picasso's development: the simplified, geometric treatment of Stein's face reflects his growing interest in Iberian sculpture and non-Western art, and it came just before his move toward Cubism.