Old English lytel "not large, not much; short in distance or time; unimportant," also used in late Old English as a noun, "small piece; a short time," from West Germanic *lutilla- (cf. Old Saxon luttil, Dutch luttel, Old High German luzzil, German lützel, Gothic leitils "little"), perhaps originally a diminutive of the root of Old English lyt "little, few," from PIE *leud- "small." "Often synonymous with small, but capable of emotional implications which small is not" [OED].
Phrase the little woman "wife" attested from 1795. Little people "the faeries" is from 1726; as "children," it is attested from 1752; as "ordinary people" (opposed to the great), it is attested from 1827. Little Neck clams (1884) are so called for Little Neck, Long Island, a "neck" of land on the island's North Shore. Little by little is from late 15c. (litylle be litille). Little green men "space aliens" is from 1950. Little black dress is from 1939.
Little Orphan Annie originally was (as Little Orphant Annie) the character in James Whitcomb Riley's 1885 poem, originally titled "Elf Child." The U.S. newspaper comic strip created by Harold Gray (1894-1968) debuted in 1924 in the New York "Daily News."