The adjective slipshod means characterised by a lack of care, thought or organisation.

The obsolete noun slip-shoe denoted a loosely fitting shoe or slipper. It is first recorded in The fardle of facions conteining the aunciente maners, customes and lawes, of the peoples enhabiting the two partes of the earth, called Affricke and Asie (London, 1555), an incomplete translation by William Waterman of the ethnographic compendium Omnium gentium mores, leges et ritus (The manners, laws and customs of all peoples – 1520), by the German humanist Johann Boemus (circa 1485-1535); the chapter titled Of Turcquie, and of the maners, Lawes, and Ordenaunces of the Turcques contains:

(1812 reprint)
House, or Churche, or any other place wher they entende to sitte, no man entreth with his shoes on. For it is compted a very dishonest and an vnmanerly facion, to sitte shoed. Wherfore they vse a maner of slippe shooes, that may lightly be putte of and on.

In the adjective slipshod, formed after the noun slip-shoe and literally meaning wearing loose shoes or slippers, shod, the past participle of the verb shoe, means wearing shoes, as in high-shod, wearing high shoes, and dry-shod, having one’s shoes dry.

In M. William Shakspeare: His True Chronicle Historie of the life and death of King Lear and his three Daughters. With the vnfortunate life of Edgar, sonne and heire to the Earle of Gloster, and his sullen and assumed humor of Tom of Bedlam (Quarto 1, 1608), the English poet and playwright William Shakespeare (1564-1616) suggested that going slipshod was suitable for persons with kibes (i.e. chilblains):

Foole. If a mans braines where in his heeles, wert not in dan-
ger of kibes? Lear. I boy.
Foole. Then I prethe be mery, thy wit shal nere goe slipshod.

The English playwright Thomas Middleton (1580-1627) also used slipshod pejoratively in his comedy Your fiue gallants (London, 1608); Goldstone says to a tailor:

Out ath’house, you slip-shood, shamlegd, browne-thred, penny-skeand rascall.

The adjective came to mean, of shoes, untidy, in bad condition, worn down at the heel. In St. Ronan’s Well (Edinburgh, 1823), the Scottish novelist Walter Scott (1771-1832) described “the learned minister of St. Ronan’s” and “the carelessness of his dress”:

Black stockings, ungartered, marked his professional dress, and his feet were thrust into the old slip-shod shoes, which served him instead of slippers.

In The Feast of the Poets (London, 1814), the poet and literary critic James Henry Leigh Hunt (1784-1859) used slipshod figuratively in the sense careless, slovenly, when writing about George Crabbe (1754-1832):

His versification, where the force of his thoughts does not compel you to forget it, is a strange kind of bustle between the lameness of Cowper and the slip-shod vigour of Churchill, though I am afraid it has more of the former than the latter.

And, in Sybil; or, The Two Nations (London, 1845), the British statesman and novelist Benjamin Disraeli (1804-81) wrote of

those middle-aged nameless gentlemen of easy circumstances who haunt clubs, and dine a great deal at each other’s houses and chambers; men who travel regularly a little, and gossip regularly a great deal; who lead a sort of facile, slipshod existence, doing nothing, yet mightily interested in what others do.