Green’s Dictionary of Slang

1. a tall hat or bonnet; thus sky-scraper/sky-scraping adj., tall (of a hat), full-length (of a garment).

1800		Sir W. Scott Letter 5 Apr. (1937) XII. 159: The trumpets call me to swagger in a cockd skyscraper and sword .
1826		C.M. Westmacott Eng. Spy II 170: Only cast off that sky scraper of yours before the boom sweeps it overboard.
1832		Currency Lad (Sydney) 3 Nov. 4/2: [A] black long-tailed coat, towing over my taffel with a sky-scraper cape.
1836		Lancaster Gaz. 12 Nov. 4/2: Boney [...] his sky-scraper crossed aloft, and [...] Wellington’s head along side of him.
1847		J.A. Eames Budget of Letters 397: She gave me a black silk bonnet [...] which stuck right up in the air after the fashion of the old ‘sky scrapers’ [DA].
1855		Bell’s Life in Sydney 7 Apr. 2/7: Den sailor pull off Missy Emma’s bonnet, and he call it coal-scuttle and sky-scraper; den him jump on top of it.
1868		Downpatrick Recorder (Down, NI) 8 Feb. 2/3: The ‘three-cornered sky scraper’ as it was facetiously called, is far more becoming [...] than the four-cornered velvet cap of the College.
a.1885		in Century Mag. (NY) XXXV 950/1: Milliner’s wire [...] was used to give outline to the skyscraper bonnets of the day [DA].
1889		‘’Arry in Parry’ in Marks ’Arry Ballads (2006) 93: It’s a bloominger sky-scraping Topper.
1890		Shrewsbury Chron. 23 May 5/5: A befitting bustle, flounced cashmere dress, a sky-scraper or coal-scuttle bonnet.
1896		Wellington Exp. (OH) 25 Mar. 3/2: The bill [...] to impose a fine upon a woman for wearing a skyscraper hat at a theater.
1899		Yorks Eve. Post 31 Aug. 2/6: What protection is afforded by a sky-scraper or a bonnet baffles a man’s ingenuity to determine.

2. a tall horse.

1826

Pierce Egan’s Life in London 491/1: All trotting down the road [...] some on great slapping nine-hand skyscrapers; some on nimble daisy-cutting nags.

3. a notably tall person.

1859, 1860		Hotten Dict. of Modern Sl. etc.
1873		Sl. Dict.
1895		C. Crowe Aus. Sl. Dict. 75: Sky Scraper, a tall person.
1908		N.Y. Times 18 Sept. in Fleming Unforgettable Season (1981) 226: After Marquard had thrown a few practice balls [...] along comes Taylor, and the skyscraper retires to the bench.

4. a rider on a ‘penny-farthing’ cycle.

1892

Daily News 7 Mar. 6/6: Riders of the ordinary [cycle] [...] are few and far between, and are often derisively styled ‘sky-scrapers’ .

5. the penis.

1890–1904

Farmer & Henley Sl. and Its Analogues.