Mary Newbolt is a sensitive, tenderly executed portrait from a formative period of Craigie Aitchison’s career. It was painted from life while both the artist and the sitter, Aitchison’s close friend Mary Newbolt, were studying at the Slade School of Fine Art. Sittings took place at the art school and there is a resemblance between this and Aitchison’s contemporaneous life-room paintings of the female nude. The colour is applied thinly, staining the pores of the coarse-grained canvas while retaining a limpid quality. The pallid skin tones are ethereal and lively and carry a suggestion of breath and vitality. The construction of the image is complete, even as the canvas is exposed in several areas. The mouth is a slender pink smudge, immediately legible but rendered with extreme brevity; underlying traces of outlines, along the jawline and in the face, indicate that the picture was initially mapped with a drawing. Exposed canvas complements the delicate style of the painting, creating a tension between literal material qualities and the smooth verisimilitude of the image. The simplicity of the drawing and the limpid intensity of the colouring are strongly prescient of the distinctive style that Aitchison later developed and made his own.

Newbolt and Aitchison were inseparable for a time at the Slade, as Aitchison’s monographer Cate Haste has described:

'Craigie had several close friends among the women students. He fell in love with Mary Newbolt: "He was absolutely mad about her. Really, really in love," Susan Ward observed. […] For nearly a year they went about together. […] Friends referred to Mary as "Craigie’s girl". Though she didn’t believe she was in love with him, she saw him as her "only real friend" at the Slade.'

In its intimate size and sympathetic handling, Aitchison’s portrait captures some of the warmth and tenderness that existed between him and Newbolt. Haste described it as ‘one of his most moving’ portraits. Newbolt later married another Slade student, Joe Hope, after Aitchison made a characteristic misreading of the emotional situation and unceremoniously ended their friendship. Having established that they did not wish to marry, he reasoned that they should sever all contact.