Green’s Dictionary of Slang

1. (also skepper) a barn.

c.1566		Harman Caveat for Common Cursetours in Viles & Furnivall (1907) 83: A Skypper, a barn.
1592		Groundworke of Conny-catching A2: I couched in a hogshead in a Skipper this darkmans.
1608		Dekker Lanthorne and Candle-Light Ch. 1: The Canters Dict. Skipper: a barne.
1610		Rowlands Martin Mark-all 43: The Clapper dugeon lies in the skipper / He dares not come out for shame.
1621		Jonson Gypsies Metamorphosed 4: ’Tis thought fit he marche in the Infants Equipage With the convoy cheates, and peckage out of the clutch of Harman-beckage, to theire Libkens at the Crackmans or some skipper of the Black-mans.
1637		Dekker Canting Song in Eng. Villainies (8th edn) O2: Store of Stroommell weele have here, and i’th skipper Lib in state.
1641		R. Brome Jovial Crew II i: Here, safe in our Skipper, let’s cly off our Peck, / And bowse in defiance o’ the Harman-Beck.
1665		Head Eng. Rogue I 52: Skepper, a Barn.
a.1674		‘The Rogues . . . praise of his Stroling Mort’ in Head Canting Academy (1674) 19: [as cit. 1637].
1688		J. Shirley Triumph of Wit 222: What, though I no Togeman wear, / Nor Commission, Mish, or Slate / Store of Strammel we’ll have here, / and in th’ Skipper lib in State.
1688		R. Holme Academy of Armory Ch. iii item 68c: Canting Terms used by Beggars, Vagabonds, Cheaters, Cripples and Bedlams. [...] Skipper, a Barn.
c.1698		B.E. Dict. Canting Crew n.p.: Skipper c. a Barn.
1707		J. Shirley Triumph of Wit (5 edn) 198: What though I no Togeman wear, / nor Commission, Mish, or Slate / Store of Strammel we’ll have here, / and in a’ Skipper lib in State [What though I no Cloak do wear, / And neither Shirt nor Sheet do bear, / Yet Straw we’ll have enough that’s sweet, And tumble when i’th’ Barn we meet].
1725		New Canting Dict. [as cit. c.1698].
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. [as cit. c.1698].
1741		Canting Academy, or the Pedlar’s-French Dict. 115: A Barn Skipper.
1754		Scoundrel’s Dict. 15: A Barn – Skipper.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1809		G. Andrewes Dict. Sl. and Cant.
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1859		Hotten Dict. of Modern Sl. etc. 94: SKIPPER, a barn. Ancient cant.
1864, 1867, 1870		Hotten Sl. Dict. [as cit. 1859].
1882		Dundee Courier 22 Sept. 7/4: There’s no such thing as a skipper till we get off the moor.
1895		Belfast News-Letter 26 Dec. 7/1: Joe, I’m done up, and can’t go any more. S’pose we hunt for a ‘skipper’.
1933		M. Marshall Tramp-Royal on the Toby 19: There was a big hayloft up under the rafters, [...] one of the cosiest skyppers it has been my lot to have dossed in.
1935		Thieves Slang ms list from District Police Training Centre, Ryton-on-Dunsmore, Warwicks 10: Skipper: A night out.

2. one who sleeps in hedges and outhouses.

1925		Flynn’s 3 Jan. 661/2: Skipper, [...] a lodging house; a tramp.
1965		Guardian 9 Dec. 9/1: It was the night of the big Government census of the ‘skippers’ – the people who sleep rough.
1977		Listener 28 July 103/3: On the rubble-strewn redevelopment sites of central Glasgow, you find the groups of ‘skippers’, the men who live rough.

3. in weak senses of sense 1, a shelter for tramps and other homeless people.

1932		M. Marshall Travels of Tramp-Royal 191: I felt more like an anchorite [...] than a twentieth century tramp dossing in a skypper.
1936		W.A. Gape Half a Million Tramps 214: A ‘skipper’ is a place where you shelter for the night without permission.
1966		G. Fletcher Down Among the Meths Men 32: The Ram would [...] cook it over the bum’s fire in the Greatorex Street skipper [...] an ancient stuccoed house in the last stages of dilapidation. [Ibid.] 54: A skipper is where the meths men, the homeless ones or bums sleep, above or below ground.
1988		J. Healy Grass Arena (1990) 122: […] Some skippers are fair; most are bad. One feature common to both – they are all lousy.
1990		J. Healy Streets Above Us (1991) 136: The hallway of the skipper is gloomy and dark.