The portrait has historical significance, due to the subject's role in Picasso's early life as a struggling artist and eventual commercial success.

She recalled how during one session, when the sittings were nearly coming to an end in the winter, Picasso suddenly painted out the head and irritably said, "I can't see you any longer when I look."

"[4] Picasso's painting challenged the traditional ideas of portraiture, by depicting the subject as a large, hulking figure who stares blankly across the image, rather than towards the viewer.

In contrast to the work of Henri Matisse, Picasso uses dark, subdued hues of brown and red, rather than bright colours to portray his subject.

This angular distortion is characteristic of his later Cubist works and is a notable contrast to the rounded, flat rendering of the rest of her body.

[6] Alfred H. Barr Jr., Director of the Museum of Modern Art, commented on the significance of the repainting of the head in Stein's portrait.

This change of style turned out to be of great historic importance for it showed the direction Picasso was to follow step by step until it led to cubism.On the portrait's importance, Alfred H. Barr Jr. remarked that, "Aside from its value as a landmark in modern art, Picasso's painting stands as a powerful characterization of one of the most remarkable and influential American writers of her generation.

"Universally recognized as one of the classic and pivotal works of Picasso's late Rose period, Portrait of Gertrude Stein brilliantly captures the psychological character of one of the great American writers and cultural figures of the last century.

"[2] In 2015, Jonathan Jones wrote: "Ever since the Renaissance, the portrayal of women had been shaped by ideals of beauty and constrained social roles.