Green’s Dictionary of Slang

1. (US) rough, heavy work boots.

1830		Mechanics’ Press (Utica, NY) 9 Jan. 66/3: In six days they crimpt and made forty-five pairs of Stoga Boots.
1847		J. Palmer Travels over Rocky Mts 104: I paid for a pair of stoga shoes, made in one of the eastern states, and a very common article, four dollars and fifty cents.
1855		Ballou's Dollar Mthly Mag. (Boston, MA) Oct. 874/2: Jim was [...] wholly absorbed in blacking a pair of stout boots [...] as if his very existence depended on raising a polish on his stogies.
1868		Horticulturalist (NY) Jan. 29/1: If it [i.e. a flower-bed] be badly cared for, woe to the boot or shoe less than a ‘stogy’ that ventures upon it.
1873		Overland Mthly Aug. 149/1: His possessions were a suit of gray tweed, a flannel shirt or two, also gray; thick stogie boots [etc].
1874		Godey’s Mag. 88-9 260: Just out in the field a-hoin’ an’ a-plowin’, in his unbleached shirtsleeves, an’ coarse butternut pants, an’ stogy shoes, all covered with mud.
1885		Overland Mthly n.d. 590: [...] followed by a pair of longer legs, encased, for the most part, in tall, stogy boots.
1895		(con. 1859) W.G. Puddefoot Minute Man of the Frontier [ebook] Men wore stogy boots, generally with one leg of the trousers outside.

2. (US) a cigar.

1869		Telegrapher 4 Dec. 114/1: Stopping at [...] Wheeling and Marietta, to renew our supply of provender and ‘stogies’.
1873		J. O’Connor Wanderings of a Vagabond 52: After the lunch, liquors and cigars (red-eye and stogies), the best the place afforded, were introduced by the host.
1897		Kipling Captains Courageous 8: He was lighting that terrible article, a Wheeling ‘stogie’.
1904		Brownsville Dly Herald (TX) 19 Nov. 2/2: One of the men rolled a leaf of tobacco in his hand and wrapped it with another leaf. That was the first stogy.
1916		C. Sandburg ‘Fellow Citizens’ Chicago Poems 21: The way he lighted a three-for-a-nickel stogie and cocked it at an angle regardless of the manners of our best people.
1929		W.R. Burnett Little Caesar (1932) 11: Vettori lit his stogie.
1930		J. Lait Gangster Girl 51: [He] then turned—ostensibly to light a stogey.
1932		(con. 1910s) J.T. Farrell Young Lonigan in Studs Lonigan (1936) 8: Old man Lonigan [...] sat tilted back in his chair, enjoying his stogy.
1939		P. Di Donato Christ in Concrete 197: Luigi removed stogie from mouth.
1948		H. McCoy Kiss Tomorrow Goodbye in Four Novels (1983) 161: He puffed on his stogie and frowned.
1952		W.R. Burnett Little Men, Big World 220: The Commissioner was smoking one of his cheap stogies, the smoke polluting the heavy air.
1961		‘M.B. Longman’ Power of Black (1962) 142: People like the look of a green leaf on a stogie Cuba style.
1970		E. Thompson Garden of Sand (1981) 106: He puffed his two-for-a-nickel stogie.
1983		N. Heard House of Slammers 34: Joe lit one of his stogies.
1998		Eble Campus Sl. Nov. 6: stoag – cigar, cigarette.
1999		Guardian Rev. 3 Dec. 43: I imagine him smoking fat stogies.
2000		Observer 16 Jan. 22: Kirsty dons a fedora and sticks a half-chewed stogie in the corner of her mouth.
2010		Codella and Bennett Alphaville (2011) 355: A cigar humidor full of expensive Cuban stogies.
2021		T. Pluck Boy from County Hell 126: [He] spat out the stogie.

3. attrib. use of sense 1.

1908		‘O. Henry’ ‘Conscience in Art’ in Gentle Grafter (1915) 129: Isn’t the entree nous into the salons of the stogie smokers going to be harder than you imagined?
1925		S. Lewis Arrowsmith 76: In its ponderous leather chairs are torn seams and stogie ashes.
1990		S. Morgan Homeboy 59: I could smell stogie tobacco, but no smoke.
2000		Indep. on Sun. Culture 14 May 18: Last week Carrie and her stogey-smoking boyfriend went to a cocktail party.

4. (US drugs) an over-sized marijuana cigarette.

1980

E. Folb Runnin’ Down Some Lines 171: You kin roll it real fat [...] like a stogie, big old tuskee.