luff n.

Old English glof "glove, covering for the hand having separate sheaths for the fingers," also "palm of the hand," from Proto-Germanic *galofo "covering for the hand" (source also of Old Norse glofi), probably from *ga- collective prefix + *lofi "hand" (source also of Old Norse lofi, Middle English love, Gothic lofa "flat of the hand"), from PIE *lep- (2) "be flat; palm, sole, shoulder blade" (source also of Russian lopata "shovel;" Lithuanian lopa "claw," lopeta "shovel, spade").

German Handschuh, the usual word for "glove," literally "hand-shoe" (Old High German hantscuoh; also Danish and Swedish hantsche) is represented by Old English Handscio (the name of one of Beowulf's companions, eaten by Grendel), but this is attested only as a proper name. Meaning "boxing glove" is from 1847. Figurative use of fit like a glove is by 1771.

1530s, "to windward," from a- (1) "on" + Middle English loof "windward direction," which is probably from Dutch loef (Middle Dutch lof) "the weather side of a ship" (see luff (n.)).

Originally in nautical orders to keep the ship's head to the wind, and thus stay clear of a lee-shore or some other quarter; hence "at a distance but within view" (1530s) and, figuratively, "apart, withdrawn, without community spirit" (with verbs stand, keep, etc.). As an adjective from c. 1600. Related: Aloofly; aloofness.