mid-13c., "tool for measuring right angles, carpenter's square," from Old French esquire "a square, squareness," from Vulgar Latin *exquadra, back-formation from *exquadrare "to square," from Latin ex "out" (see ex-) + quadrare "make square, set in order, complete," from quadrus "a square" (from PIE root *kwetwer- "four").

Meaning "square shape or area" is recorded by late 14c. (Old English used feower-scyte). Geometric sense "four-sided rectilinear figure" is from 1550s; mathematical sense of "a number multiplied by itself" is first recorded 1550s. Sense of "open space in a town or park" is from 1680s; that of "area bounded by four streets in a city" is from c. 1700. As short for square meal, from 1882. Square one "the very beginning" (often what one must go back to) is from 1960, probably a figure from board games.

early 14c., "containing four equal sides and right angles," from square (n.), or from Old French esquarre, past participle of esquarrer. Meaning "honest, fair," is first attested 1560s; that of "straight, direct" is from 1804. Of meals, from 1868.

Sense of "old-fashioned" is 1944, U.S. jazz slang, said to be from shape of a conductor's hand gestures in a regular four-beat rhythm. Square-toes meant nearly the same thing late 18c.: "precise, formal, old-fashioned person," from the style of men's shoes worn early 18c. and then fallen from fashion. Squaresville is attested from 1956. Square dance attested by 1831; originally one in which the couples faced inward from four sides; later of country dances generally.

[T]he old square dance is an abortive attempt at conversation while engaged in walking certain mathematical figures over a limited area. [The Mask, March 1868]

in geometry, "quadrilateral plane figure having all its angles right and all its opposite sides equal," 1570s, from French rectangle (16c.), from rect-, combining form of Latin rectus "right" (from PIE root *reg- "move in a straight line," with derivatives meaning "to direct in a straight line") + Old French angle (see angle (n.)). Late/Medieval Latin rectiangulum meant "a triangle having a right angle," noun use of neuter of rectiangulus "having a right angle." When the adjacent sides are equal, it is a square, but rectangle usually is limited to figures where adjacent sides are unequal.