'Portrait of Vanessa Bell (The Red Hat)' is a significant, large-scale painting of Duncan Grant’s fellow painter and life-long partner. The image is composed using a painterly method in which the entire surface is animated by the legible application of paint. Aside from the hands, which are detailed with sinuous outlines, the picture emerges from a continuous screen of pure colour in which the contrast of neighbouring colours creates both the modelling of light and shade and the sense of shape and volume. The green walls beside the figure contrast with the sitter’s red hat and dress, serving the pictorial function of propelling her forwards in space. The textures of clothing, skin and furnishings are suppressed to exaggerate the facture of the painting. Notwithstanding the prominence of the stylish, handicraft mark making, the sitter is invested with a strong sense of personality. The catchlights in her eyes are a luminous, resonant shade of vermilion. The dress that Bell wears was made by a dressmaker from a roll of red velvet that she bought herself, and the present work is the only depiction of Bell in this red cloche hat. The cloche hat had been invented in 1908 by the milliner Caroline Reboux, but became particularly popular around 1918 and into the 1920s.

Bell sat for Grant on several other occasions in this period, and the resulting pictures are among the artist’s most insightful and characteristic. This portrait was painted at Charleston, the Sussex farmhouse that Grant and Bell moved to in 1916. According to the Bloomsbury Group specialist Richard Shone, it is almost certainly the second portrait that Grant painted of her there. The first was painted in 1917. 'Portrait of Vanessa Bell' is painted on a substantial, thick-panelled board of wood. Grant enjoyed using heavy wooden surfaces as the support for his paintings when he first moved to Charleston, and Shone has suggested this portrait was painted on part of a door from the farmhouse.

A number of similarities are apparent between 'Portrait of Vanessa Bell' and Paul Cézanne’s 'Madame Cézanne in a Red Dress'. In both Grant and Cézanne’s paintings, the sitter wears a maroon-coloured dress, set against a pale green interior wall, with an embroidered drapery hanging prominently to one side of the composition. In both works, the characterisation of the sitter is ambivalent and sullen. It is likely that Grant was familiar with Cézanne’s painting, which was available to him through a reproduction in Ambroise Vollard’s illustrated monograph about Cézanne. The French artist’s painting of his wife was perhaps invested with special poignance owing to Grant and Bell’s heightened intimacy at this time: their daughter Angelica was conceived around the time of the painting’s execution. Cézanne was highly regarded by others in Grant and Bell’s circle, including John Maynard Keynes, who purchased Cézanne’s still life of apples from the Degas sale in March 1918, and Roger Fry, who later wrote an influential monograph about the artist.