leeway (n.)

Middle English le, leoh, from Old English hleo "shelter, cover, defense, protection," from Proto-Germanic *khlewaz (source also of Old Norse hle, Danish læ, Old Saxon hleo, Dutch lij "lee, shelter"). The original sense is uncertain; it might have been "warm" (compare German lau "tepid," Old Norse hly "shelter, warmth"), and Watkins traces it to a PIE *kle-wo-, a suffixed variant form of the root *kele- (1) "warm."

Nautical sense "that part of the hemisphere to which the wind is directed" (c. 1400) is of Scandinavian origin, from the notion of the side of the ship opposite that which receives the wind as the sheltered side. As an adjective, 1510s, from the noun. The lee shore is that toward which the wind blows. Middle English also had lewth "warmth, shelter," Old English hleowþ, with Proto-Germanic abstract noun suffix *-itho (see -th (2)). Also compare lukewarm.

Old English weg "road, path; course of travel; room, space, freedom of movement;" also, figuratively, "course of life" especially, in plural, "habits of life" as regards moral, ethical, or spiritual choices, from Proto-Germanic *wega- "course of travel, way" (source also of Old Saxon, Dutch weg, Old Norse vegr, Old Frisian wei, Old High German weg, German Weg, Gothic wigs "way"), from PIE root *wegh- "to go, move, transport in a vehicle."

From c. 1300 as "manner in which something occurs." Adverbial constructions attested since Middle English include this way "in this direction," that way "in that direction," both from late 15c.; out of the way "remote" (c. 1300). In the way "so placed as to impede" is from 1560s.

From the "course of life" sense comes way of life (c. 1600), get (or have) one's way (1590s), have it (one's) way (1709). From the "course of travel" sense comes the figurative go separate ways (1837); one way or (the) other (1550s); have it both ways (1847); and the figurative sense of come a long way (1922).

Adverbial phrase all the way "completely, to conclusion" is by 1915; sexual sense implied by 1924. Make way is from c. 1200. Ways and means "resources at a person's disposal" is attested from early 15c. (with mean (n.)). Way out "means of exit" is from 1926. Encouragement phrase way to go is short for that's the way to go.

c. 1300, "main road, highway," from Old English heafodweg; see head (adj.) + way (n.). Sense of "motion forward" first attested 1748, short for ahead-way; ultimately nautical (compare leeway).