hard-boiled, adj. — Green’s Dictionary of Slang

hard-boiled adj.

1. tough, mean, unpleasant.

1903		O. Wister Philosophy 4 20: ‘The duality, or multiplicity, of the ego.’ ‘The hard-boiled ego,’ commented the boy with the ruler.
1918		letter in K.F. Cowing Dear Folks at Home (1919) 4: Gun-totin’, rip-roarin’, son-of-gun of a hard-boiled Marine that I am.
1921		P. & T. Casey Gay-cat 235: Oh, he’s hard-boiled, thet kid [...] He’s bin workin’ with a nortorious [sic] yegg afore this.
1930		E. Glyn Flirt and Flapper 57: Flapper: Some of our Grannies are as hard-boiled as us.
1932		Edinburgh Eve. News 6 Sept. 2/5: Music is a passion with these hard-boiled miners and factory workers.
1936		R. Chandler ‘Guns At Cyrano’s’ in Red Wind (1946) 213: A hard-boiled redhead sang a hard-boiled song in a voice that could have been used to split firewood.
1936		Wodehouse ‘Tried in the Furnace’ in Young Men in Spats 49: There is something about evening church in a village in the summer-time that affects the most hard-boiled.
1943		Mass-Observation Report on Juvenile Drinking 11: Blacks, sailors, soldiers (Canadian and American) frequent this pub. Women mostly 30–40, hard-boiled types.
1953		J. Thompson Savage Night (1991) 66: Tell me you haven’t been leading me on, acting hardboiled and easy to get.
1966		C. Himes Run Man Run (1969) 95: Don’t talk so vulgarly [...] You’re always trying to be hard-boiled.
1989		H. Rawson Dict. of Invective (1991) 366: A soft-boiled fellow is easygoing, naïve, or impractical, in contrast to a tough, hard-boiled type.
1999		Guardian Guide 29 May–4 June 63: Chandler fell under the influence of Dashiell Hammett, modelling his hard-boiled, gun-toting sleuth on Hammett’s Sam Spade.
2005		P. Swirski From Lowbrow to Nobrow 140: The 1950s did mark the twilight of the hardboiled tradition.

2. (US) used as intensifier.

1907

Eve. Statesman (Walla Walla, WA) 5 Mar. 3/2: Remarking that Blinks has Jinks [...] beat to a frazzle, or a hard-boiled frazzle.

SE in slang uses

In compounds

hard-boiled collar (n.)

a stiff, starched, detachable collar.

1925		S. Lewis Arrowsmith 55: I will not put on a hard-boiled collar! I won’t!
1953		J. Thompson Savage Night (1991) 83: He was all duked out in a hard-boiled collar and a blue serge suit.

hard-boiled hat (n.) (also hard-boiled lid)

(US) a stiff hat.

1885		Arizona Champion 16 May 3/2: Bob, that hard boiled hat will have to be dispensed with if you intend to live in Winslow.
1888		Arizona Champion 10 Mar. 4/1: Hard boiled hats were at a discount Wednesday evening. Several dudes lost their starched tiles in a game of football.
1899		Mohave County Miner 10 June 3/3: Jack Poland distinguished himself [...] by shaving off hi whiskers and donning a hard-boiled hat.
1903		A. Adams Log of a Cowboy 127: That fellow in front of the drug store over there, with the hard-boiled hat on.
1914		A.P. Man Jr ‘Further Word-List – Arizona’ in DN IV:ii 165: hard-boiled hat, n. Derby?
1915		S. Ford Torchy, Private Sec. 178: From a hasty glimpse at the hard-boiled lid and the man’s collar [...] I thought it was some chappy.
1917		B.M. Bower Lookout Man 95: One is one of them schoolma’ms that goes around in a boiled shirt and a hard-boiled hat.
1922		P.A. Rollins Cowboy 106: The Range knew that the city-dwellers wore also ‘hard’ or ‘hard-boiled’ hats.
1954		Collans & Sterling House Detectives 100: Pictures typed the house officer as a poker-faced joker wearing a hard-boiled hat, a suspicious scowl and a well-gnawed cigar butt [HDAS].

hard-boiled shirt (n.) (also hard-boiled chest protector) [ext. of boiled shirt under boiled adj.]

(US) a stiff, starched detachable shirt front.

1911		G. Bronson-Howard Enemy to Society 158: Mostly they wore hard-boiled shirts, originally white, creased of bosom, unclean of cuffs.
1913		Tacoma Times (WA) 10 July 4/4: Every guy what gets into the blow-out has to doll up in a hard-boiled chest protector.
1921		Dundee Courier 27 June 4/5: A multi-millionaire is obliged to put on a hard-boiled shirt every evening.
1927		C. Hamilton Caste 300: Outwardly neat in a blue serge suit, [...] a black satin tie with a pearl pin, a hard-boiled shirt, and shoes.
1931		W.N. Burns One-Way Ride 86: He remained hard-boiled even in a hard-boiled shirt.
1934		A. Halper Foundry 406: A white shirt with a hard-boiled front.