Origin and history of outwit

"inward awareness of right or wrong" (a word formed to translate Latin conscientia), early 13c., "conscience;" c. 1300, "reason, intellect," from in (adj.) + wit (n.).

Þese ben also þy fyve inwyttys: Wyl, Resoun, Mynd, Ymaginacioun, and Thoght [Wycliffe, c. 1380]

Not related to Old English inwit, which meant "deceit." Joyce's use of it in "Ulysses" (1922) echoes the title of the 14c. work "Ayenbite of Inwyt" ("Remorse of Conscience," a translation from French) and is perhaps the best-known example of the modern use of the word as a conscious archaism, but it is not the earliest.

If ... such good old English words as inwit and wanhope should be rehabilitated (and they have been pushing up their heads for thirty years), we should gain a great deal. [Robert Bridges, English poet laureate, 1922]

"mental capacity, the mind as the seat of thinking and reasoning," Old English wit, witt, more commonly gewit "understanding, intellect, sense; knowledge, consciousness, conscience," from Proto-Germanic *wit-, which is reconstructed to be from PIE root *weid- "to see," metaphorically "to know" (also compare wit (v.) and wise (adj.)).

The meaning "ability to connect ideas and express them in an amusing way" is recorded by 1540s, hence "quickness of intellect in speech or writing" (for nuances of usage, see humor (n.)). The sense of "person of wit or learning" is attested from late 15c.

To be at one's wit's end "perplexed, at a loss" is from late 14c. Witjar was old slang (18c.) for "head, skull." Witling (1690s) was "a pretender to wit." Witword was "testament." Also in Middle English of the sensitive faculty generally, and sensory impressions, as wittes five for the five bodily senses (c. 1200).

Germanic cognates include Old Saxon wit, Old Norse vit, Danish vid, Swedish vett, Old Frisian wit, Old High German wizzi "knowledge, understanding, intelligence, mind," German Witz "wit, witticism, joke," Gothic unwiti "ignorance."

A witty saying proves nothing. [Voltaire, Diner du Comte de Boulainvilliers]

Wit ought to be five or six degrees above the ideas that form the intelligence of an audience. [Stendhal, "Life of Henry Brulard"]

in Old English a common prefix with nouns, adjectives, adverbs, and verbs, "out, outward, outer; forth, away," from out (adv.). The use was even more common in Middle English, and also with the senses "outer, outside, on the outside, from without, external, externally; apart; greatly, extremely; completely, thoroughly, to completion." Other senses of out that extended into the use as a prefix include "beyond the surface or limits; to the utmost degree; to an explicit resolution."

In composition out has either its ordinary adverbial sense, as in outcast, outcome, outlook, etc., or a prepositional force, as in outdoors, or forms transitive verbs denoting a going beyond or surpassing of the object of the verb, in doing the act expressed by the word to which it is prefixed, as in outrun, outshine, outvenom, etc. In the last use especially out may be used with almost any noun or verb. [Century Dictionary]