"piece of shaped cloth spread so as to catch the wind and cause a vessel to move in water," Old English segl "sail, veil, curtain," from Proto-Germanic *seglom (source also of Old Saxon, Swedish segel, Old Norse segl, Old Frisian seil, Dutch zeil, Old High German segal, German Segel), of obscure origin with no known cognates outside Germanic (Irish seol, Welsh hwyl "sail" are Germanic loan-words). In some sources (Klein, OED) referred to PIE root *sek- "to cut," as if meaning "a cut piece of cloth."
As "a single ship or vessel" by 1510s. To take the wind out of (someone's) sails (1888) is to deprive (someone) of the means of progress, especially by sudden and unexpected action, "as by one vessel sailing between the wind and another vessel" ["The Encyclopaedic Dictionary," 1888].
Old English segilan "travel on water in a ship by the action of wind upon sails; equip with a sail," from the same Germanic source as sail (n.); cognate with Old Norse sigla, Middle Dutch seghelen, Dutch zeilen, Middle Low German segelen, German segeln. Later extended to travel over water by steam power or other mechanical agency. The meaning "to set out on a sea voyage, leave port" is from c. 1200. Extended sense of "float through the air; move forward impressively" is by late 14c., as is the sense of "sail over or upon." Related: Sailed; sailing.
1670s, probably from lug (n.) in some obscure sense; perhaps so called from the "ear" of sail formed by the oblique hang of the yard from the mast.
Old English seglinge, "act of one who or that which sails," verbal noun from the source of sail (v.). Gradually coming also to mean "the art or rules of directing a ship." Figurative use of smooth sailing for "easy progress" is from 1840.
Yes; I must press on this marriage; Georgina has not wit enough to manage him—at least till he's her husband, and then all women find it smooth sailing. [Bulwer Lytton, "Money: A Comedy in Five Acts," 1840]
c. 1400, sailer, "one who sails," agent noun from sail (v.). The spelling with -o-, erroneous but now established, arose 16c., probably by influence of tailor, etc., and to distinguish the meaning "seaman, mariner" from "thing that sails."
It replaced much older seaman and mariner (q.q.v.), and its later appearance is perhaps to avoid confusion with common Middle English saillour, sailer "dancer, tumbler, acrobat" (mid-13c. as a surname), from Old French sailleor (from Latin salire "to leap"). Old English also had merefara "sailor."
Applied as an adjective from 1870s to clothing styles and items based on a tailor's view of a sailor's characteristic attire. Vulgar extended form sailorman is by 1761. Sailor's purse "egg pouch of a ray or shark" is so called by 1874; it is typically empty when found on shore.