Why do people refer to cigars as “stogies”?
My Concise Oxford Dictionary reads thus:
Stogy, -gie, (gi) n Rough heavy boot, long narrow roughly made cigar. [orig, stoga, short for Conestoga in Pennsylvania]
Your guess is as good as mine on this one. I would venture that the wet and shredded cigar butt might have the appearance of a soggy boot (especially if the cigar were kinked from being stubbed out). How to link a cigar to a covered wagon is another matter entirely.
Never heard the boot definition. But I know about the cigars.
Back in the old days, cigars were not the big fat things we know today from cartoons and gangster movies. They were actually rather thin and small.
Wagon drivers headed west (Conestoga wagon drivers) wanted a somewhat more substantial smoke–one that they could light and put in their mouth and enjoy for an hour or more. For these wagon drivers, cigar makers created bigger and fatter cigars that became known as “conestogas,” after the wagons. The name became shortened to “stogie” through use.
Cigars today have a variety of names that denote a size: Churchill, corona, petit-corona, robusto, and so on; and although I don’t know for sure, I’d guess that the term “conestoga” might have once denoted a standard size as well. But today, “stogie” is just a term meaning a cigar.