Green’s Dictionary of Slang

rich; financially secure.

1824		Pierce Egan’s Life in London 24 Oct. 4/3: It was a drawing room touch altogether: the swell was accomodated in elegant style ; the well-breech’d Gents. as comfortable as they could wish.
1827		Egan Anecdotes of the Turf, the Chase etc. 181: Harry, in general, was ‘better breeched’ than his rivals.
1833		‘The Cly-Pecker’ in Swell!!! or, Slap-Up Chaunter 38: A strumpet approach’d with a tipsy young squire – / She knock’d, when the bawd from within, I heard say, / ‘If he’s green, and well-breech’d, I will knock up a fire.’.
1887		G. Devol Forty Years a Gambler 142: I told him that I had a man for him who was well heeled.
1893		J. Hawthorne Confessions of Convict 145: She was well-heeled.
1906		O.W. Hanley ‘Dialect Words From Southern Indiana’ in DN III:ii 123: well heeled, adj. Well to do; in good circumstances.
1908		L.W. Payne Jr ‘Word-List From East Alabama’ in DN III:iv 286: all-heeled, adj. Well provided for, all right. ‘Don’t you worry about me. I’m all-heeled.’.
1929		W.R. Burnett Little Caesar (1932) 238: I’m pretty well heeled right now and I’m looking for a place to lay in.
1936		J. Curtis Gilt Kid 51: He had done a gaff and was well heeled with dough.
1939		D. Burley N.Y. Amsterdam News 24 June 16: They’ll [i.e. fight fans] come [...] well ‘heeled’.
1946		R. Brister ‘Fake It Easy’ in Mammoth Mystery June 🌐 He [...] always tried to keep well-heeled. You never knew when you’d have to buy your way out of trouble.
1955		D. Niland Shiralee 76: Macauley knew the shearers were well-heeled.
1964		P. Highsmith Two Faces of January (1988) 11: It was not a place for the well-heeled, not a place the average American would be drawn to.
1977		B. Davidson Collura (1978) 106: 50 smartly dressed, well-heeled patrons.
1988		D. Woodrell Muscle for the Wing 7: The gentlemen who had assembled [...] were well dressed, well fed, and well heeled.
1996		(con. 1964-65) B. Thorpe Sex and Thugs and Rock ’n’ Roll 30: By my standards they were well-heeled.
1997		A. Highcrest At Home on the Stroll 127: Devlin was young, white and well-heeled.
2000		Indep. 7 Feb. 18: A kind and well-heeled friend got me into one of those corporate hospitality box affairs.
2012		T.P. McCauley ‘Lady Madeline’s Dive’ in ThugLit Sept./Oct. [ebook] ‘Any smart guy would’ve laughed in your face, but a couple of well-heeled dopes like them’.
2024		J. Meades Empty Wigs (t/s) 309: Well heeled! Once upon a time only the rich wore high heels.