Etymology
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Words related to less

little (adj.)

Old English lytel "not large, not much, small in size or number; short in distance or time; unimportant,"

from Proto-Germanic *lutilla- (source also of Old Saxon luttil, Dutch luttel, Old High German luzzil, German lützel "little"), perhaps originally a diminutive of the root of Old English lyt "little, few," from PIE *leud- "small."

"Often synonymous with small, but capable of emotional implications which small is not" [OED]. Now with less, least, but formerly and in dialect littler, littlest. In terms of endearment from 1560s. Meaning "younger" (of a brother, sister, etc.) is from 1610s. As an adverb, Old English lytel.

Little while "a short time" is from 12c. Phrase the little woman "wife" attested from 1795. Little people "the faeries" is from 1726; as "children" it is attested from 1752; as "ordinary people" (opposed to the great) from 1827. Little death "orgasm" (1932) translates French petite mort. Little Neck clams (1884) are so called for Little Neck, a "neck" of land on Long Island's North Shore, where they first came into favor. Little green men "space aliens" is from 1950. Little boys' room (or girls') as a euphemism for "lavatory" is from 1957. Little breeches for "boy" is by 1785. Little black dress is from 1939.

At the beginning of summer, smart women who stay in town like to wear sheer "little black dresses." Because most "little black dresses" look alike, retailers struggle each year to find something which will make them seem new. [Life magazine, June 13, 1939]
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unless (conj.)

mid-15c., earlier onlesse, from (not) on lesse (than) "(not) on a less compelling condition (than);" see less. The first syllable originally was on, but the quality of negation in the word and the lack of stress changed it to un-. "Except could once be used as a synonym for unless, but the words have now drawn entirely apart" [Century Dictionary].

least (adj.)
Old English læst, earlier læsest "smallest, lowest in power or position" (superlative of little (adj.)), from Proto-Germanic superlative *laisista-, from PIE root *leis- (2) "small" (see less). Qualifying phrase at least "not to say more than is certainly true" is Middle English æt læstan, from the notion of "at the lowest degree." As a noun, "smallest admissible quantity or degree," from early 12c.; as an adverb, Old English læst "in the least degree."
lessen (v.)
"to become less," c. 1300, from less (adj.) + -en (1). Transitive sense "to make less" is from c. 1400. Related: Lessened; lessening.
lesser (adj.)

early 13c., a double comparative, from less (adj.) + -er (2). Johnson calls it "a barbarous corruption of less, formed by the vulgar from the habit of terminating comparatives in -er." As an adverb from 1590s; now generally poetic or obsolete except in expressions such as lesser-known (1813) and lesser of two evils.

lest (conj.)
c. 1200, "that not," especially "for fear that" [OED calls it a negative particle of intention], from a contraction of the Old English phrase þy læs þe "the less that," from þy, instrumental case of demonstrative article þæt "that" + læs (see less) + conjunction þe (see the). The þy was dropped and the remaining two words contracted into early Middle English leste.