This oil on canvas marked a significant change in the direction of portrait painting. Completed in 1906, the subject sat for the artist a reported 80 or 90 times – although this is believed by some to be an exaggeration – before he painted over the face and abandoned the work declaring ‘I cannot see you any longer’.

Picasso returned to the canvas one year later, and completed the portrait quickly without further sittings. Despite criticism from many who thought the painting didn’t look like Stein, she liked her portrait and kept it until her death in 1946 when she bequeathed it specifically to the Metropolitan Museum of Art where it still hangs.

Gertrude Stein was an American writer born in 1874 who moved to Paris in 1903 with her brothers. The family collected art, especially works by Henri Matisse, and they set up a literary salon in the French capital that was very popular amongst the literary elite.

The salon was a meeting place for people such as Ernest Hemingway, F. Scott Fitzgerald and Matisse as well as other influential figures of the arts.

Stein was also introduced to Alice Toklas at the salon in 1907 and the two became partners soon after. The pair were inseparable for the rest of their lives, and Stein even wrote a book about her partner.

Picasso, originally from Malaga in Spain, moved to Paris in 1904 and met Stein just one year later when she was 30 and he 24, and a close friendship was soon established. She commissioned her portrait not long after they met, and Picasso was excited and keen to capture her formidable personality.

The Portrait of Gertrude Stein is important because it demonstrates signs of the initial beginnings of Cubism – the art style which is attributed to Picasso.

Cubism was founded in 1907 by Picasso and Georges Braque and is an abstract style using geometric shapes and showing several views of a person or object in a single painting. In the Stein portrait, the body has been painted in a more natural style, with some details picked out in the fabric of the chair, but in contrast the face stands out due to its mask-like quality.

There are elements of slight distortion in the face, one side looking as though it is captured from a different view point, demonstrating early beginnings of the Cubism style that is to follow. The face in the painting is smooth, with dark outlines around the eyes; these are characteristics that get carried through to Picasso's later paintings.

In Demoiselles D’Avignon, for example, the two central figures have the same outlined eyes and the simple eyebrows look similar to the Stein portrait.

In fact the hair also looks identical in both of these paintings - scraped back in a bun and placed on top of the head almost like a hat. Looking at the painting as a whole, Picasso highlights some of the Stein’s well-known personality traits in this portrait. The subject is seated in a strong, more masculine pose.

She is leaning forward and filling the canvas and the viewer gets the feeling that this is a sturdy woman who is powerful and confident. Although she looks serious, there is no feeling of anger in the piece, in fact the painting seems positive in its emotion. These are the attributes of Stein that Picasso wanted to capture and share with his audience, and the ones the sitter was most pleased with.