"in a satisfactory manner," Old English wel "abundantly, very, very much; indeed, to be sure; with good reason; nearly, for the most part," from Proto-Germanic *wel- (source also of Old Saxon wela, Old Norse vel, Old Frisian wel, Dutch wel, Old High German wela, German wohl, Gothic waila "well"), from PIE root *wel- (2) "to wish, will" (source also of Sanskrit prati varam "at will," Old Church Slavonic vole "well," Welsh gwell "better," Latin velle "to wish, will," Old English willan "to wish;" see will (v.)).
Also used in Old English as an interjection and an expression of surprise. The adjective was in Old English in the sense "in good fortune, happy," from the adverb; sense of "satisfactory" is from late 14c.; "agreeable to wish or desire" is from mid-15c.; "in good health, not ailing" is from 1550s. Well-to-do "prosperous" is recorded by 1794.
by c. 1200 as an emphatic form of Old English of (see of), employed in the adverbial use of that word. The prepositional meaning "away from" and the adjectival sense of "farther" were not firmly fixed in this variant until 17c., but once they were they left the original of with the transferred and weakened senses of the word. Meaning "not working" is from 1861.
Off the cuff "extemporaneously, without preparation" (1938) is from the notion of speaking from notes written in haste on one's shirt cuffs. In reference to clothing, off the rack (adj.) "not tailored, not made to individual requirements, ready-made" is by 1963, on the notion of buying it from the rack of a clothing store; off the record "not to be publicly disclosed" is from 1933; off the wall "crazy" is 1968, probably from the notion of a lunatic "bouncing off the walls" or else in reference to carom shots in squash, handball, etc.
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Definitions of well-off from WordNet
in fortunate circumstances financially; moderately rich;