He was educated at St Paul's School, London, and then at Balliol College, University of Oxford, where he read classics.

His major work was The Modern Movement in Art[4] (1927) which he dedicated to Geoffrey Faber who had encouraged him to write it.

[5][1] All his books were aimed at the educated layman and showed his journalistic ability to convey his meaning using catchy phrases, periodisation, and easily understood language.

His views were described by Peter Stewart of the University of Oxford as "remarkable" and "damn[ing] the art of the ancients by taking it out of the hands of the connoisseurs and dilettante".

[6] In 1933 he produced John Ruskin: An Introduction to Further Study of his Life and Work in which he attempted a psychological interpretation of Ruskin's life and work, arguing that he was a manic-depressive and mentally unwell from his early years, but acknowledging that he (Wilenski) had no qualifications in the field of mental health.