Green’s Dictionary of Slang

(orig. US black) a hat with a narrow brim.

1905		Courier-Jrnl (Louisville, KY) 7 May 19/2: [advert] The Golf Yachts, with the new 3-inch brims [...] we show all the correct things in ‘stingy-brim’ yachts.
[1906		Chicago Trib. 4 Nov. 58/1: Have you seen Frank Comerford’s new hat? It’s a black Fedora with a stingy-brim].
1920		Nebraska State Jrnl (Lincoln, NE) 6 June 18/4: When his fellow citizens wore bonnets with stingy brims [...] Father would [...] appear in a wideawake.
1931		Pensacola News-Jrnl (FL) 5 Sept. 5/8: [advert] Have you seen the new stingy-brim felt hats?
1934		Z.N. Hurston Jonah’s Gourd Vine (1995) 164: Okay, stingy papa. You eben wear uh stingy-rim hat.
1949		‘Hal Ellson’ Duke 94: I saw a sweet stingy-brim in which I would look fine.
1950		‘Hal Ellson’ Tomboy (1952) 93: He’s a real sharp dresser [...] Did you see that brown tweed coat and that black short-brim he wore?
1957		H. Simmons Corner Boy 24: He [...] placed a gray stingy brim on his head.
1964		R. Abrahams Deep Down In The Jungle 38: The baboon stood with a crazy rim. / Charcoal grey vine with a stingy brim.
1965		W. King ‘The Game’ in King Black Short Story Anthol. (1972) 306: He was neat from toe to stingy.
1971		D. Goines Dopefiend (1991) 182: He broke the stingy brim down.
1979		New Musical Express 17 Nov. n.p.: A pair of dark glasses, maybe a stingy brim hat, with an inch-wide brim.
1980		E. Folb Runnin’ Down Some Lines 110: Sharkskin suit, stingy brim, else fedora.
1990		N. George ‘Gangsta Attitude’ in Buppies, B-Boys, Baps and Bohos (1994) 125: New jacks sporting ’70s pimp hats and ’50s old school gangster stingy-brims.
2001		C. Sheridan Brilliant Corners 130: Monk showed up sporting a mean goatee and a Stingy-brim hat that was so Chicago.
2017		D. Winslow The Force [ebook] On his head, even in summer, is his trademark trilby, with its stingy brim and a red feather on the left side.