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Origin and history of stogie
stogie(n.)
also stogy, type of large cheap cigar, 1869, colloquial; the word is attested by 1835 as an adjective meaning "rough, heavy, coarse" (of work shoes, etc.); also of cigars, "long, cheap" (1861); it is based on variant shortenings of Conestoga, the name of an important agricultural region near Lancaster, Pennsylvania. Both items were so-called because favored by drivers of the Conestoga style of covered wagons that were associated with that region (which also was noted for a breed of strong horses).
As a noun, stoga for "rough boot" is by 1830. Also compare Jamieson's Scottish dialectal stoggie "rough in a general sense," of cloth, "coarse and rough" (1825).
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