c. 1200, "opposite of right," probably from Kentish and northern English forms of Old English *lyft "weak; foolish" (in lyft-adl "lameness, paralysis"). Compare East Frisian luf, Dutch dialectal loof "weak, worthless").
Sense of "opposite of right" is from the left being usually the weaker hand), a derived sense also found in cognate Middle Dutch and Low German luchter, luft. Compare Lithuanian kairys "left" and Lettish kreilis "left hand" both from a root that yields words for "twisted, crooked."
The usual Old English winstre/winestra "left" (adj.); "left hand," literally "friendlier," a euphemism used superstitiously to avoid invoking the unlucky forces connected with the left side (compare sinister). The Kentish word itself might have been originally a taboo replacement, if instead it represents PIE *laiwo- "considered conspicuous" (represented in Greek laios, Latin laevus, and Russian levyi). Greek also uses a euphemism for "left," aristeros "the better one" (compare also Avestan vairyastara- "to the left," from vairya- "desirable").
Meaning "being on the left-hand side" is from c. 1300. As an adverb from early 14c. For political senses, see left (n.). Used at least since c. 1600 in various senses of "irregular, illicit;" earlier proverbial sense was "opposite of what is expressed" (mid-15c.), for example over the left (shoulder) "not at all," added to a statement to negate or neglect what was just said (1705). To have two left feet "be clumsy" is attested by 1902.
Phrase out in left field "out of touch with pertinent realities" is attested from 1944, from the baseball fielding position that tends to be far removed from the play (left field in baseball attested by 1867; the fielding positions are from the point of view of the batter). The Parisian Left Bank (of the River Seine) has been associated with intellectual and artistic culture at least since 1893; Left Coast "Pacific Coast of the U.S." is by 1980s.
German link, Dutch linker "left" are said to be not directly related to these, being instead from Old High German slinc and Middle Dutch slink "left," related to Swedish linka "limp," slinka "dangle," and Old English slincan "crawl" (Modern English slink).
Old English understandan "to comprehend, grasp the idea of, receive from a word or words or from a sign the idea it is intended to convey; to view in a certain way," probably literally "stand in the midst of," from under + standan "to stand" (see stand (v.)).
If this is the meaning, the under is not the usual word meaning "beneath," but from Old English under, from PIE *nter- "between, among" (source also of Sanskrit antar "among, between," Latin inter "between, among," Greek entera "intestines;" see inter-). Related: Understood; understanding.
That is the suggestion in Barnhart, but other sources regard the "among, between, before, in the presence of" sense of Old English prefix and preposition under as other meanings of the same word. "Among" seems to be the sense in many Old English compounds that resemble understand, such as underniman "to receive," undersecan "examine, investigate, scrutinize" (literally "underseek"), underðencan "consider, change one's mind," underginnan "to begin."
It also seems to be the sense still in expressions such as under such circumstances. Perhaps the ultimate sense is "be close to;" compare Greek epistamai "I know how, I know," literally "I stand upon."
Similar formations are found in Old Frisian (understonda), Middle Danish (understande), while other Germanic languages use compounds meaning "stand before" (German verstehen, represented in Old English by forstanden "understand," also "oppose, withstand"). For this concept, most Indo-European languages use figurative extensions of compounds that literally mean "put together," or "separate," or "take, grasp" (see comprehend).
The range of spellings of understand in Middle English (understont, understounde, unþurstonde, onderstonde, hunderstonde, oundyrston, wonderstande, urdenstonden, etc.) perhaps reflects early confusion over the elements of the compound. Old English oferstandan, Middle English overstonden, literally "over-stand" seem to have been used only in literal senses.
By mid-14c. as "to take as meant or implied (though not expressed); imply; infer; assume; take for granted." The intransitive sense of "have the use of the intellectual faculties; be an intelligent and conscious being" also is in late Old English. In Middle English also "reflect, muse, be thoughtful; imagine; be suspicious of; pay attention, take note; strive for; plan, intend; conceive (a child)." Also sometimes literal, "to occupy space at a lower level" (late 14c.) and, figuratively, "to submit." For "to stand under" in a physical sense, Old English had undergestandan.