Green’s Dictionary of Slang

1. a male scion of the British upper classes; prob. wealthy, certainly well-connected, but essentially devoid of intelligence or ‘character’.

[1881		Voice (N.Y.) 17 Mar. 5/4: A nation of chinless men without opinions [OED]].
1906		Appleton’s Mag. 8 527: His chin — had he possessed one — would, no doubt, have been equally insignificant; but he was renowned, from Mombasa to the Sabi-mouth and far inland, as the Chinless Wonder.
1918		J.M. Grider War Birds (1926) 73: The Chinless Wonder and Dora and Peggy were all there.
1920		in A. Cornebise Amaroc News (1981) 24 Feb. 87: Those ‘eggheads certain chinless chappies and fairy wonders who hid behind petticoats to avoid French mud monkey meat and slum and German machine guns’.
1934		F. Merrill Kippy of the Cavendish 147: Her inimitably told story of the latest escapade of some prince or duke, her adoring approval of the Chinless Wonder as he ordered another magnum.
1940		Western Dly Press 9 Jan. 6/4: Lord Haw-Haw, the Chinless Wonder of the German Broadcasting station.
1956		J. Osborne Look Back in Anger Act I: Brother Nigel? The straight-backed, chinless wonder from Sandhurst?
1959		G. Slatter Gun in My Hand 127: Windy Wilkinson the wingless wonder.
1967		J. Burke Till Death Us Do Part 90: We don’t need a lot of chinless wonders sitting up in the House of Lords.
1968		(con. 1940s) G. Dutton Andy 19: [of airmen in prison] Aren’t you two wingless wonders coming?
1979		F. Norman Too Many Crooks Spoil the Caper 44: The sort of boys I went out with used to take me to tarted-up pubs [...] full of musak and Axeminster and chinless wonders talking bullshit.
1985		B. Humphries Traveller’s Tool 132: A couple of years ago I had the onerous job of showing some chinless wonder from England over the Australian outback.
1993		K. Lette Foetal Attraction (1994) 57: His guest, a cravated Chinless Wonder.
2000		Guardian Editor 17 Mar. 18: He called the soldiers ‘chinless wonders’.

2. attrib. use of sense 1.

1929

S.J. Perelman Dawn Ginsbergh’s Revenge 187: That chinless wonder boy friend of hers.