Born to Galician Jewish parents in Romania in 1892, Clare Winsten (née Clara Birnberg) immigrated to England with her family c. 1902. A member of the Women’s Freedom League, she was also the only girl among the 'Whitechapel Boys', a group of artists and poets linked through the East End Jewish community centred around Whitechapel and Stepney. The latter included her future husband Stephen Winsten (formerly Samuel ‘Simy’ Weinstein), the poet/publisher John ‘Jimmy’ Rodker, and Joseph Leftwich (who coined the name), as well as the painter/poet Isaac Rosenberg and painters Mark Gertler and David Bomberg, whom she studied alongside at the Slade School of Fine Art. Her work was included in the so-called ‘Jewish Section’ co-curated by Bomberg and Jacob Epstein as part of the Whitechapel Art Gallery’s ‘Twentieth-Century Art: A Review of Modern Movements’ in 1914. Bomberg painted her and she and Rosenberg created reciprocal portraits.
During the First World War, the Winstens, were Pacifists, Conscientious Objectors and members of the 'No Conscription' fellowship. They married in 1916 and in November of the same year, Stephen Winsten undertook the first of three consecutive terms of imprisonment for his beliefs. Postwar both worked on humanitarian causes and became Quaker Humanists. Stephen Winsten published a book of poems ‘Chains’ (1920), for which Clare produced a number of (unpublished) illustrations, based on his prison experience. Clare Winsten's output included drawings, paintings and sculpture including several of George Bernard Shaw, their neighbour at Ayot St Lawrence, Hertfordshire, in the late 1940s, about whom Stephen wrote a number of books.
Winsten’s work is held by the British Museum, the National Portrait Gallery, UCL and the Harry Ransom Humanities Research Centre, University of Texas at Austin.