Green’s Dictionary of Slang

(US) too short, usu. of trousers, occas. of other clothing or hair; thus highwaters n., trousers that are too short.

1856		‘Mark Twain’ Adventures of Snodgrass 9: Then some soldiers with bob-tailed tin coats on (high water coats we used to call ’em in Keokuk) come in, then some gals (with high water dresses on).
1881		Lancaster Daily Intelligencer (PA) 28 Dec. 3/7: They Need Their high Water Pants [...] The Hudson is more than eight feet above lwo water level.
1883		Bourbon News (Millersburg, KY) 6 Mar. 1/2: Who stole Ed Ryan’s high-water pants?
1896		Courier (Lincoln, Neb.) 27 June 1/2: Mr Brown rushes to a newspaper office [...] and hitching up his high-water pants, shouts [etc.].
1899–1900		C.L. Cullen Tales of the Ex-Tanks 239: You ought to have seen the rig he put on me then – the high-water boys that only reached to my shoe tops.
1902		C.L. Cullen More Ex-Tank Tales 139: A mastodonic Rube [...] wearing high water trousers.
1911		S. Ford Torchy 285: How is it up there in the opodeldoc zone that they can get these high-water pant legs to fit so much like lengths of stovepipe?
1911		E.B. Morris Senior 5: Costumes [...] Beane Act I, high-water trousers, collar too big, trousers one pattern.
1918		(con. 1899) E.S. O’Reilly Roving and Fighting 7: Groups of soldiers greeted us [...] with sarcastic humor. ‘Look at the Johnny-come-latelies!’ ‘Get on to the guy with the high-water pants!’.
1922		B. Hecht A Thousand and One Afternoons [ebook] Mr. Martin [...] slipped from the window ledge, shaking down his wrinkled, high-water pants.
1933		Hecht & Fowler Great Magoo 61: He is dressed in a very old suit of an era that went in for wasp waists and high-water pants.
1949		A.I. Bezzerides Thieves’ Market 136: He was dressed in a cheap imitation tweed suit that was tight across the shoulders and ‘high-water’ at the shoes.
1950		WELS [DARE].
c.1960		Wilson Collection n.p.: High-water pants or high waters. . . A boy’s pants after they have shrunk or he has grown, or both, so that they seem to have been cut in time of high water [DARE].
1972		B. Rodgers Queens’ Vernacular 106: pants which are too short for the wearer [...] high-water.
1978		E.S. Katz Folklore 27: When a person wears pants so short they’d be good for wading home in a downpour, have you heard them teasingly called floods or high water britches?
1982		G. Sculatti Catalog of Cool 116: Worn cuffless at ‘high-water’ levels, exposing [...] sock [...] between shoe top and pant bottom.
1989		(con. 1960s) M. Kingston Tripmaster Monkey 5: You wouldn’t mislike them on sight if their pants weren’t so highwater, [...] F.O.B. fashions—highwaters or puddlecuffs.
1992		D. Pinckney High Cotton (1993) 85: They had my sisters’ permission to make comments about my ‘high-water’ trousers. They said my cuffs fell so high above my shoes I wouldn’t have to roll them up in a flood.
2003		J. Lethem Fortress of Solitude 61: Wrong sneakers, wrong shoes, wrong length of pants. Highwaters.