Green’s Dictionary of Slang

skipper (it) v.

to sleep rough.

1858		A. Mayhew Paved with Gold 267: She had caught an ague from ‘skippering it,’ that is, sleeping under haystacks.
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor III 405/2: We used to meet a great many on the road [...] and sometimes we used to stop and skipper with them of a night. Skippering is sleeping in barns or under hedges.
1873		Sl. Dict.
1891		F.W. Carew Autobiog. of a Gipsey 413: A rough lot they were [...] reg’lar keyhole whistlers the lot of ’em, skipperin’ it for choice when they’d got the price of a doss about ’em.
1931		E. Blair letter 4 Sept. in Complete Works X (1998) 228: As to new words, here are some [...] Skipper, to = to sleep in the open.
1933		‘George Orwell’ Down and Out in Complete Works I (1986) 176: These (omitting the ones that everyone knows) are some of the cant words now used in London: [...] To skipper – to sleep in the open.
1967		Glatt et al. Drug Scene in Grt Britain 117: Skipper – to sleep one night and move on.
1971		E.E. Landy Underground Dict. (1972) 170: skipper v. [...] sleep rough.
1981		T. Wilkinson Down and Out 55: You can go skippering, sleeping in derelict houses.
1988		J. Healy Grass Arena (1990) 93: He was a middle-aged Jock, used to travel out on the last tube to Edgeware every night to skipper.