So just a little something I learned in my History of Costume course-- in the late 1700's to mid-1800's, fashionable men's shoes had heels, buckles, and square toes. Then this style went out of style, but was continued to be worn by older, more conservative men who rejected the styles the young whippersnappers were picking up. Thus, these men began to be called "square-toes", which has since evolved into our slang term of "square: a boring, stifling, inside-the-box person."
Who knew?!
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