Michael Fane arrives in the thin red house in Carlington Road to his new family of Nurse, Cook, Annie the housemaid, his younger sister Stella, and the occasional presence of Mother. From here, the novel follows the next twenty years of his life as he tries to find his place in the upper echelons of Edwardian society, through prep school, studies at Oxford, and his emergence into the wide world. The setting is rich in period detail, and the characters portrayed are vivid and more nuanced in their actions and stories than first impressions imply.

Sinister Street was an immediate critical success on publication, although not without some worry for its openness to discuss less salubrious scenes, and it was a favorite of George Orwell and John Betjeman. Compton Mackenzie had attended both St. James’ school and St. Mary’s College at Oxford and the novel is at least partly autobiographical, but for the same measure was praised as an accurate portrayal of that experience; Max Beerbohm said “There is no book on Oxford like it. It gives you the actual Oxford experience.” Although originally published in two volumes (in 1913 and 1914) for commercial reasons, the two form a single novel and have been brought back together again for this edition.