Manuscripts, correspondence, financial and legal documents, address books, and personal papers make up the Gertrude Stein Collection. The material was collected by Alice B. Toklas after Stein's death and includes a large amount of Toklas's incoming correspondence. The collection is arranged in four series: I. Works, 1930-1945 (1 box); II. Correspondence, 1928-1946 (1 box); III. Personal Papers, 1914-1959 (1 box); and IV. Alice B. Toklas, 1920-1973 (bulk 1947-1967) (6 boxes).

Stein's writings are represented by three titles in the Works series. was originally a lecture delivered at Oxford and Cambridge in 1926; later that year it appeared in and in book form from Leonard and Virginia Woolf's Hogarth Press. is a two-page depiction of couturier Pierre Balmain that appeared in in 1945. The dossier of items relating to the publication of documents not only various stages in Stein's creation of this work, but also the conflicts between Stein and Georges Hugnet, whose collection of French poems, , was originally to have been published along with Stein's. The two disagreed over whether Stein's work was a translation of Hugnet's or an original work loosely based on it and could not come to an agreement on how the two authors should be credited in the book. Also included are letters from composer Virgil Thomson, who had introduced them to each other in 1927, trying to reconcile their differences.

The Correspondence series contains a large number of Stein's letters to Hugnet from the period of their first acquaintance until their final break. Incoming letters are concerned with matters of publication and include correspondence from her American publisher, Random House, and her English agents, Pearn, Pollinger & Higham, Ltd. (later known as David Higham Associates, Ltd.). All correspondence in this and other series is arranged alphabetically by author or recipient.

Among the Personal Papers are an address book, various contracts, and miscellaneous financial records. Of particular interest in this series are documents concerning Stein's art collection: two insurance policies (dated 1935 and 1938) with Lloyds of London with itemized schedules and appraisals of the paintings, and three appraisals made for Alice Toklas after Stein's death (1958 and undated).

The largest series is devoted to Alice B. Toklas. It includes a few random pages from autobiographical writings; a small number of letters to other correspondents, either drafts or returned letters; an address book and other personal and financial papers; and a large incoming correspondence from such writers as literary agent Mrs. William Aspenwall Bradley, actor Sandy Campbell, historian Bernard Faÿ, Stein scholar Donald C. Gallup, attorneys Edgar Allan Poe and Russell M. Porter, composer Virgil Thomson, and writer Carl Van Vechten, who served as Stein's literary executor. Many of these letters, mostly dating from the last few years of Toklas's life, are filled with expressions of concern for the state of her health or her misfortune in losing Gertrude Stein's art collection to the Stein family. Letters to Toklas's companion, Madeleine Charrière, have been interfiled with those to Toklas herself, and a few of these letters are dated after Toklas's death. A peculiarity of this collection is that Toklas herself evidently made a practice of ripping up letters once she had answered them; approximately one-third are torn into large pieces. Fortunately, all the pieces have been preserved. Among the personal papers are a very small number of recipes, some in Toklas's hand, and transcripts of letters written by admirers of Stein on the occasion of the exhibit organized in 1965 in Paris by the American Cultural Center.