outsmart (v.)

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]

Middle English smert, from late Old English smeart, in reference to hits, blows, etc., "stinging; causing a sharp pain," related to smeortan "be painful" (see smart (v.)). The adjective is not represented in the cognate languages.

Of speech or words, "harsh, injurious, unpleasant," c. 1300; thus "pert, impudent; on the impertinent side of witty" (by 1630s). In reference to persons, "quick, active, intelligent, clever," 1620s, perhaps from the notion of "cutting" wit, words, etc., or else "keen in bargaining."

From 1718 in cant as "fashionably elegant;" by 1798 as "trim in attire," "ascending from the kitchen to the drawing-room c. 1880" [Weekley]. For sense evolution, compare sharp (adj.); at one time or another smart also had the extended senses in sharp.

Attested from late 12c. as a surname, earlier as a component in them, including Christiana Smartknave (1279). In reference to devices, the sense of "behaving as though guided by intelligence" is attested by 1972 (smart bomb, also the computing smart terminal). The figurative smart cookie "clever, perceptive person" is from 1948.