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).
c. 1200, "the left-hand side, the side opposite the right," from left (adj.). In military formations with reference to the center; of river banks it implies going in the direction the current flows; in an assembly in reference to the seat of the presiding officer; in baseball in reference to the point of view of the batter.
Political sense "the democratic or liberal party" arose from the custom of assigning those members of a legislative body to the left side of a chamber. This usage is first attested in English in 1837 (by Carlyle, in reference to the French Revolution), and probably is a loan-translation of French la gauche (1791), said to have originated during the seating of the French National Assembly in 1789 in which the nobility took the seats on the President's right and left the Third Estate to sit on the left. The term became general in U.S. and British political speech c. 1900. Century Dictionary and OED 2nd ed. both refer to this as primarily in reference to continental European politics.