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Apr 29, 2026
This week’s theme
Geometrical terms used figuratively

This week’s words
squarehead
circle the wagons
square-toed

square-toed
“Only You Can Stop Square-Toe Shoes Syndrome” (1 min)
Video: GQ

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square-toed

PRONUNCIATION:
(skwair-tohd)

MEANING:
adjective: Old-fashioned or conservative.

ETYMOLOGY:
From square, from Latin exquadrare (to square) + toe, from Old English ta (toe). Earliest documented use: 1785.

NOTES:
The word square has had both flattering and unflattering careers. It can suggest honesty and fairness, as in a square deal or fair and square. But it can also imply rigidity, conventionality, and a lack of swing. In jazz-era slang, square came to mean unhip, possibly from a conductor’s boxy four-beat motions.

A square-toed shoe, once literally fashionable, later came to suggest someone whose tastes had stayed planted while fashion walked on. That helped give square-toed its figurative sense: old-fashioned, conservative, and stiff in manner or outlook.

USAGE:
“’In England the climate is so atrocious that the people become grim-visaged and square-toed through constantly watching the rain coming down. Or else,’ he added, with another suppressed ripple of that infectious laugh of his, ‘the climate in England has become so atrocious because there are so many square-toed folk about.’”
Emma Orczy; The First Sir Percy; Hodder & Stoughton; 1920.

See more usage examples of square-toed in Vocabulary.com’s dictionary.

A THOUGHT FOR TODAY:
I don't need time. What I need is a deadline. -Duke Ellington, jazz pianist, composer, and conductor (29 Apr 1899-1974)

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