23.4.2.2 OUTLINES (from Turabian 9th edition)
In some situations, you may include an outline or a similar enumeration in an appendix to your paper, or in a draft stage of the paper (see 6.2.1). Use the following system of notation, consisting of letters and roman and Arabic numerals, and indent each level by one further tab (usually a half-inch). You should have at least two items to list at each level; if you do not, reconsider the structure of the outline. If the items are phrases, capitalize them sentence-style (see 22.3.1) and do not use terminal punctuation. If they are complete sentences, capitalize and punctuate them as you would any other sentence (see 6.2.1 for an example).
I. Wars of the nineteenth century
A. United States
1. Civil War, 1861–65
a) Cause
(1) Slavery
(a) Compromise
i) Missouri Compromise
ii) Compromise of 1850 . . .
b) Result
II. Wars of the twentieth century
A. United States
1. First World War . . .
Source
Turabian, Kate L.. A Manual for Writers of Research Papers, Theses, and Dissertations, Ninth Edition (Chicago Guides to Writing, Editing, and Publishing) (p. 341). University of Chicago Press. Kindle Edition.