Alfred Chester, the youngest of three children, was born on September 7, 1928, in Brooklyn, New York. His father, Jake, a Jewish furrier and proprietor of the Alfred Fur Company, came to the United States as a child from Romania, his family name Americanized from Chesta-Polchak or Chestya-Pelski by immigration authorities. His mother, Anna Chester, was born in Odessa. Chester is reported to have had a comfortable childhood, despite the Great Depression and his status as the son of an immigrant.

Chester's central literary theme, of otherness or isolation, is thought to have been fostered by an illness which struck him in his seventh year, resulting in hair loss. Lack of eyelashes, eyebrows, head and body hair created an awkward appearance which Chester refused to publicly acknowledge, even to close friends. Although his Jewish background did not seem to create personal conflict, his artistic sensibility, homosexuality, and appearance did. The orange, bedraggled wig coupled with denial of his physical condition that persisted until the age of 36, made him feel and look the part of the outsider.

In 1945, Chester enrolled in Washington Square College of the New York University, contributing to and (all NYU publications), and took his B.A. in English in 1949. He attempted graduate study at Columbia University, but abandoned it in 1950 and began travelling, first with a short visit in Mexico. Then, armed with a collection of completed short stories, he moved on to France, and eventually to Morocco. His French foray lasted the better part of the 1950s--and established Chester as a familiar cafe presence, providing him the opportunity to discover and shape his style and craft, and to meet with publishers and other literary minds including Carson McCullers, Mary Louise Aswell, James Baldwin, Richard Seaver, Robert Silvers, and Princess Marguerite Caetani.

Chester's association and extensive correspondence with Princess Caetani resulted in publication of his essay in in 1952, followed in that same year by publication of the Southern-Gothic short story in Chester's eccentric, existential works, a popular style in the mid-50s, attracted attention. The publication of a collection of short stories, sold by subscription by the Silver's Editions Finisterre in Paris, garnered him the recognition of V.S. Pritchett of the BBC who called Chester an exciting talent: original, fearless and very capable. The Paris publishing house, Editions du Seuil and soon afterwards, Andre Deutch Limited of London, published Chester's first novel, in French and English respectively. The novel, introduced in New York by The Vanguard Press in 1957, created little fanfare in America as the public's current taste favored a more realistic writing style. However, his somewhat lackluster American debut was offset by a Guggenheim Fellowship in 1957 and publication of the short story, which received the honor of inclusion in

In 1959 the purchased his short story, which financed Chester's return to the United States. In 1961 Chester's short story was published in magazine and printed in Chester finally began to enjoy a measure of popularity, and was published in the and However it was not for his fiction that Chester would be recognized.

Alfred Chester ultimately gained notoriety in America for literary criticism. His critical works, published in the and along with a regular column in established his reputation, and he was hailed for his authoritative voice and clear literary vision by popular figures such as Gore Vidal. Although he reluctantly continued his critical writing for financial reasons, Chester returned to Morocco in June 1963 to remove himself from the New York literary scene and concentrate on writing fiction. The publication of (1964) and (an experimental novel eventually published in 1967), generally disappointed and confused reviewers and the literary public.

Coinciding with the pervasive influence of Paul and Jane Bowles during Chester's Moroccan years (1963-1965), Chester's productivity dropped and his mental health suffered. His forced expulsion by Moroccan authorities in 1965, due to his extremely erratic behavior, landed him back in New York. His remaining literary contributions, written during a period charcterized by increasing dementia and geographical wandering until his death in 1971, consisted of a few short stories, semi-autobiographical essays, and fiction collected in and the clearly autobiographical an account of his travels to Israel (collected in ).