Green’s Dictionary of Slang

hobnail n.

a rustic, a simpleton.

1608		Dekker Belman of London F2: The honest Hob-nayle-wearer, can by no meanes be brought to remember this newe friend.
c.1620		Fletcher Women Pleased II vi: The hobnaile thy husband’s as fitly out o’ th way now.
1640		T. Heywood Love’s Mistress IV i: Here’s a clown for hob nailes.
1663		‘News from Chelmsford’ in Ebsworth Bagford Ballads (1878) II 738: Till he found that Hobnail’s house.
1691		‘The New Medley of the Country man, etc.’ in Ebsworth Merry Drollery Compleat (1875) 182: Good Bumkin forbear, Such hopnails as you do seldom come here.
c.1698		B.E. Dict. Canting Crew n.p.: Hobnail [...] a High-shoon or Country Clown.
1705		E. Hickeringill Priest-Craft I 13: Then, replied Hob-nails, how is it possible that there could be either Night or Day, when there was neither Sun, Moon, nor Stars.
1713		W. King York Spy 46: He is, says my Friend, a meer Hobnail, one in whom Nature, when she made his Head, forgot to put Brains.
1725		New Canting Dict. [as cit. c.1698].
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. [as cit. c.1698].
1748–49		Cleland Memoirs of a Woman of Pleasure (1985) 19: He supposed I had left my maidenhead with some hobnail in the country.
1770		Bath Chron. 12 Apr. 4/1: Says old Hobnail to Giles [...] Here comes my Lord Mayor.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue.
1798		Sporting Mag. Dec. XIII 173/2: Hold, Zur, says hobnail.
1811		Lex. Balatronicum.
1821–5		‘Bill Truck’ Man o’ War’s Man (1843) 202: Was it like a gentleman, to burst in upon us like a country hobnail.
1832		J. Miller Complete Jest Book 143: ‘We are conjurors, young hobnail!’ said the gentlemen, laughing.
1859		Matsell Vocabulum.
1905		Little Falls Herald (MN) 31 Mar. 3/3: How to Operate the Shell Game with Profit [...] When [the victim] is up against it good and cops the wrong nut, have the staller readyto split him from any hobnails that come up to knock.
1942		Berrey & Van den Bark Amer. Thes. Sl. §391.3: rustic, bumpkin, hobnail.

In compounds

hobnail hop (n.)

(US) a dance.

1938

Eve. Post (Wellington) 25 Jan. 8/8: Modern Americanisms [...] Naturally you would sooner go to a ‘hob-nail hop’ [unaccompanied] by an ‘alarm clock’.