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.