St Cyprian's was an expensive and exclusive preparatory school for boys, founded in 1899, which operated in the early twentieth century in Eastbourne, East Sussex, England. Like similar preparatory schools, its purpose was to train students to do well enough in the examinations (usually taken around the age of 12) to gain admission to Eton, Harrow, and other leading 'public schools' (as the most exclusive private secondary schools are known in England).

St Cyprian's was run by Mr. Vaughan Wilkes (the Headmaster, nicknamed 'Sambo' by the students), and his wife (nicknamed 'Flip'), and was attended, among others, by George Orwell, Cyril Connolly, and Cecil Beaton. Mrs. Wilkes is alleged to be one of the characters on which Big Brother, from the novel Nineteen Eighty-Four, is based. Orwell wrote scathingly and bitterly of his experiences at St. Cyprian's in an autobiographical essay ironically entitled 'Such, Such Were the Joys,' which was published after his death (with the name of the school changed to 'Crossgates'). Connolly described the school in somewhat less negative terms in his book The Enemies of Promise, where it is identified as 'St Wulfric's.'

In 'Such, Such Were the Joys,' Orwell recalls the colors of the old boys' tie (the necktie that the alumni of a school wear to identify themselves as such) as 'dark green, pale blue and black, if I remember rightly.'

References

• Bernard Crick, George Orwell: A Life, 1980.
• Cyril Connolly, The Enemies of Promise, 1948.
• George Orwell, "Such, Such Were the Joys." First published in the Partisan Review Sep.-Oct. 1952.