Green’s Dictionary of Slang

a smart, fashionable person.

1789		G. Parker Life’s Painter 149: Rolling Joe. A kind of fellow who dresses smart, or what they term natty.
1889–90		Barrère & Leland Dict. of Sl., Jargon and Cant.

(UK Und.) a dandified thief.

1791		H. Lemoine ‘Education’ in Attic Misc. 116: And while his flaming mot was on the lay, / With rolling kiddies, Dick would dive and buz.
c.1800		‘The Rolling Kiddy’ in Holloway & Black I (1975) 233: O this is the way to be a rolling Kiddy O.
1809		Morn. Post 4 Dec. 3/3: he entered the office with the manners [...] of what is generally termed a jolly dog, or knowing one, and by some he would have been called a rolling kiddy.
1812		Vaux Vocab. of the Flash Lang. in McLachlan (1964) 248: kiddy: a thief of the lower order, who, when he is breeched, by a course of successful depredation, dresses in the extreme of vulgar gentility, and affects a knowingness in his air and conversation, which renders him in reality an object of ridicule; such a one is pronounced by his associates of the same class, a flash-kiddy or a rolling-kiddy.
1824		‘Sonnets for the Fancy’ Egan Boxiana III 622: [as 1791].
1830		Egan Finish to the Adventures of Tom and Jerry (1889) 175: The slouched, castor, the open breeches at the knees, the short jacket, the fogle loosely twisted round his squeeze, the large wedge broach, the long-quartered shoe and silver buckles, the bit of myrtle in his gig, and the cut altogether of a ‘rolling kiddy.’.
1844		Leeds Times 22 June 6/1: Aye Jack, thou wert a rollin kiddy once, / And nearly wert thou lagged for doing the panny.