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Origin and history of leery

leery(adj.)

"knowing, wide-awake, untrusting, suspicious, alert," 1718, originally slang, with -y (2), but otherwise of unknown origin. Perhaps from dialectal lere "learning, knowledge" (see lore), or from leer (v.) in a now-obscure sense "walk stealthily with averted looks, sneak away" (1580s). OED suggests connection with archaic leer (adj.) "empty, useless," a general Germanic word (cognate with German leer, Dutch laar), of unknown origin.

also from 1718

Entries linking to leery

leer(v.)

1520s, "to look obliquely" (since 18c. usually implying a lustful, wolfish, malicious intent), probably from Middle English noun ler "cheek," from Old English hleor "the cheek, the face," from Proto-Germanic *hleuza- "near the ear," from *hleuso- "ear," from PIE root *kleu- "to hear." If so, the notion is probably of "looking askance" (compare the figurative development of cheek). Related: Leered; leering.

lore(n.)

Old English lar "learning, what is taught, knowledge, science, doctrine; art or act of teaching," from Proto-Germanic *laisti- (compare Old Saxon lera, Old Frisian lare, Middle Dutch lere, Dutch leer, Old High German lera, German Lehre "teaching, precept, doctrine"), from PIE root *lois- "furrow, track;" compare learn.

-y(2)

very common adjective suffix, "full of, covered with, or characterized by" the thing expressed by the noun, Middle English -i, from Old English -ig, from Proto-Germanic *-iga-, from PIE -(i)ko-, adjectival suffix, cognate with elements in Greek -ikos, Latin -icus (see -ic). Germanic cognates include Dutch, Danish, German -ig, Gothic -egs.

It was used from 13c. with verbs (drowsy, clingy), and by 15c. with other adjectives (crispy). Chiefly with monosyllables; with more than two the effect tends to become comedic.

Variant forms in -y for short, common adjectives (vasty, hugy) helped poets after the loss of grammatically empty but metrically useful -e in late Middle English. Verse-writers adapted to -y forms, often artfully, as in Sackville's "The wide waste places, and the hugy plain." (and the huge plain would have been a metrical balk).

After Coleridge's criticism of it as archaic artifice, poets gave up stilly (Moore probably was last to make it work, with "Oft in the Stilly Night"), paly (which Keats and Coleridge himself had used) and the rest.

Jespersen ("Modern English Grammar," 1954) also lists bleaky (Dryden), bluey, greeny, and other color words, lanky, plumpy, stouty, and the slang rummy. Vasty survives, he writes, only in imitation of Shakespeare; cooly and moisty (Chaucer, hence Spenser) he regards as fully obsolete. But in a few cases he notes (haughty, dusky) they seem to have supplanted shorter forms.