Series II: Loose Envelopes and Stationery includes 2,506 envelopes stored in boxes; these envelopes are sorted thematically by image. If the image is the same, the envelopes are stored by poetry, statement, or slogan written on the envelope. Caricatures are integrated into the categories. Thematic categories include: African American; Canons; Confederacy; Cotton; Eagles; Flags; Government; Jeff Davis; Lady Liberty; Military; Monuments: North-South Conflict; Portraits; Secession; Shields; States, Confederate; States, Union; and Union; and Miscellaneous.

Several of the envelopes were created in series; Charles Magnus was famous for his battle scenes series, printed in both black and white and in bronze, for which he would typically print 12 envelopes. Another series represented in this series is The House That ‘Uncle Sam’ Built, which is a series of 10 envelopes, based on the The-House-That-Jack-Built.

Stationery sheets are decorated at the top with images similar to those on the envelopes. Abraham Lincoln, several generals, Lady Liberty, and flags are represented on the pages. One sheet of Confederate stationery and envelopes with no image are also included. Box 17, Folder 6 includes an example of the packaging in which assorted civil war envelopes were sold; the images on the front of the envelope identify the types of envelopes originally enclosed in the package.