It was the only picture mentioned in her will. These two portraits of poet, collector, and salonnière Gertrude Stein were painted within months of each other. Left: Pablo Picasso (Spanish, 1881-1973). Gertrude Stein, 1905-6. Oil on canvas, 39 3/8 x 32 in. (100 x 81.3cm).. Gertrude Stein (1905-06) Artist: Pablo Picasso. Arguably one of Pablo Picasso's most well-known portraits, Stein is depicted with hair pulled tightly into a bun and dressed in a brown corduroy suit which was the "uniform" that made her stand out from the crowd in the streets, galleries and cafes of Paris.

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Pablo Picasso, Portrait of Gertrude Stein, oil on canvas, 1906 (Metropolitan Museum of Art) In 1905, at the same time that Leo Stein bought Matisse's Bonheur de Vivre, Gertrude commissioned a portrait by Picasso. The related story goes like this: Stein sat for Picasso so many times (supposedly 90 sittings) that eventually he said that he.. Use of Line in Pablo Picasso, Portrait of Gertrude Stein, 1905-06, oil on canvas, 100 x 81.3 cm (The Metropolitan Museum of Art, New York; photo: Steven Zucker, CC BY-NC-SA 2.0) Legacy and Influence. The "Portrait of Gertrude Stein" by Pablo Picasso is a masterwork that continues to reverberate through the history of art, embodying the transformative power of portraiture in Western art.