The collection consists chiefly of letters to Winkler, Elisa von der Recke, and others. Also included are manuscripts of some original poems, a few printed works by and about Winkler, copies of documents pertaining to Winkler's family, including Festschriften in his honor, and photographic reproductions of portraits and drawings. Correspondents include H. C. (Hans Christian) Andersen, Sarah Austin, Ludwig Börne, Eduard Devrient, Johann Peter Eckermann, Paul Johann Anselm Ritter von Feuerbach, Christian Fürchtegott Gellert, Johann Wilhelm Ludewig Gleim, Ottilie von Goethe, Karl Gutzkow, E. T. A. Hoffman, August Wilhelm Iffland, Friedrich Maximilian Klinger, August von Kotzebue, Johann Caspar Lavater, Charles Joseph, prince de Ligne, Schnorr von Carolsfeld, Ludwig Tieck, Carl Maria von Weber.
The collection contains a variety of design-related printed ephemera collected by William Drenttel and Jessica Helfand in the course of their work as principals of Winterhouse Design and later Winterhouse Institute.
The collection contains published as well as archival materials relating to the life and works of Ezra Winter (1886-1949). The collection reflects research undertaken by Jessica Helfand for the "Ezra Winter Project," a visual biography of Ezra Winter published online in 12 parts with Design Observer, the leading international graphic design blog of which Helfand is a founding editor.