Etymology
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stroll (v.)
c. 1600, a cant word introduced from the Continent, probably from dialectal German strollen, variant of Swiss German strolchen "to stroll about, loaf," from Strolch "vagabond, vagrant," also "fortuneteller," perhaps from Italian astrologo "astrologer." Related: Strolled; strolling.
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tramp (n.)
"person who wanders about, idle vagrant, vagabond," 1660s, from tramp (v.). Sense of "steamship which takes cargo wherever it can be traded" (as opposed to one running a regular line) is attested from c. 1880. The meaning "promiscuous woman" is from 1922. Sense of "a long, toilsome walk" is from 1786.
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erratic (adj.)
late 14c., "wandering, moving," from Old French erratique "wandering, vagrant" (13c.) and directly from Latin erraticus "wandering, straying, roving," from erratum "an error, mistake, fault," past participle of errare "to wander; to err" (see err). Sense of "irregular, eccentric" is attested by 1841. The noun is from 1620s, of persons; 1849, of boulders. Related: Erratically.
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beach-comber (n.)

1840 [Dana, "Two Years Before the Mast"], from beach (n.) + agent noun from comb (v.). Defined in "Century Dictionary" [1900] as "A seafaring man generally, of vagrant and drunken habits, who idles about the wharves of seaports; used most frequently in countries bordering on the Pacific ocean."

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drifter (n.)

1864, as a mining term for one who excavates "drifts" (in the specialized sense of "horizontal passages"); by 1883 as "boat fishing with drift-nets;" agent noun from drift (v.). Meaning "vagrant, man following an aimless way of life" is from 1908.

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vagabond (n.)
c. 1400, earlier wagabund (in a criminal indictment from 1311); see vagabond (adj.). Despite the earliest use, in Middle English often merely "one who is without a settled home, a vagrant" but not necessarily in a bad sense. Notion of "idle, disreputable person" predominated from 17c.
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dell (n.2)

rogue's cant 16c.-17c. for "a wench, a young girl of the vagrant class," 1560s, of uncertain origin.

A Dell is a yonge wenche, able for generation, and not yet knowen or broken by the vpright man. ... [W]hen they have beene lyen with all by the vpright man then they be Doxes, and no Dells. [Thomas Harman, "A Caveat or Warning for Common Cursitors," 1567]
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harlot (n.)
c. 1200 (late 12c. in surnames), "vagabond, man of no fixed occupation, idle rogue," from Old French herlot, arlot "vagabond, tramp, vagrant; rascal, scoundrel," with cognates in Old Provençal (arlot), Old Spanish (arlote), and Italian (arlotto), but of unknown origin. Usually male in Middle English and Old French. Used in positive as well as pejorative senses by Chaucer; applied in Middle English to jesters, buffoons, jugglers, later to actors. Secondary sense of "prostitute, unchaste woman" probably had developed by 14c., certainly by early 15c., but this was reinforced by its use euphemistically for "strumpet, whore" in 16c. English translations of the Bible. The word may be Germanic, with an original sense of "camp follower," if the first element is hari "army," as some suspect.
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rogue (n.)

1560s, "idle vagrant, sturdy beggar, one of the vagabond class," a word of shadowy origin, perhaps a shortened form of roger (with a hard -g-), thieves' slang for a begging vagabond who pretends to be a poor scholar from Oxford or Cambridge, which is perhaps an agent noun in English from Latin rogare "to ask." Another theory [Klein] traces it to Celtic (compare Breton rog "haughty"); OED says, "There is no evidence of connexion with F. rogue 'arrogant' " (the theory supported in Century Dictionary).

By 1570s, generally, as "dishonest, unprincipled person, rascal." In slight playful or affectionate use, "one who is mischievous," 1590s. Meaning "large wild beast living apart from the herd" is by 1859, originally of elephants. As an adjective, in reference to something uncontrolled, irresponsible, or undisciplined, by 1964. Also common in 17c. as a verb. Rogue's gallery "police collection of mug shots of notorious law-breakers" is attested from 1859.

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Jack 

masc. proper name, attested by 1218, probably via Anglo-French Jake, Jaikes, from Old French Jacques (which was a diminutive of Latin Jacobus; see Jacob), but in English the name always has been regarded as a familiar form of John, and some have argued that it is a native formation. In Middle English spelled Jakke, Jacke, etc., and pronounced as two syllables ("Jackie").

In England, Jack became a generic name applied familiarly or contemptuously to anybody (especially a young man of the lower classes) from late 14c. Later used especially of sailors (1650s; Jack-tar is from 1781); Jack-ashore (adj.) "drinking and in high spirits, recklessly spending" (1875) also is an image from sailors (1840 as a book title). In U.S., as a generic name addressed to an unknown stranger, attested from 1889. Every man Jack "everyone" is from 1812. Also see jack (n.).

Used in male personifications from 15c.; first record of jack-of-all-trades "person handy at any kind of work or business" is from 1610s; Jack Frost is from 1826; Jack-nasty "a sneak or sloven" is from 1833 (Jack-nasty-face, a sea-term for a common sailor, is from 1788). Jack Sprat for a small, light man is from 1560s (his opposite was Jack Weight). Jack-pudding "comical clown, buffoon" is from 1640s. Jack-Spaniard is from 1703 as a Spaniard, 1833 as "a hornet" in the West Indies. Other personifications listed in Farmer & Henley include jack-snip "a botching tailor," Jack-in-office "overbearing petty official" (1680s), Jack-on-both-sides "a neutral," Jack-out-of-doors "a vagrant" (1630s), jack-sauce "impudent fellow" (1590s).

The U.S. plant jack-in-the-pulpit (Indian turnip) is attested by 1833. Jack the Ripper was active in London 1888. The Scottish form is Jock (compare jockey (n.)). Alliterative coupling of Jack and Jill is from 15c. (Iakke and Gylle, Ienken and Iulyan). Jack Ketch for "hangman, executioner" (1670s) is said to be from the name of a public executioner in the time of James II (compare Derrick); it also was used as a verb meaning "to hang."

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