Green’s Dictionary of Slang

designating the social élite, pertaining to the wealthy.

1798		Annals 5th Congress 1948: If they wished to place them in a ridiculous point of view, or to procure for them the name of the Silk Stocking Company, or any other term of derision, they could not take a more effectual course to obtain it [DA].
1812		T. Jefferson Writings XIII 163: I trust [...] the Gores and Pickerings will find their levees crowded with silk stocking gentry, but no yeomanry [DA].
c.1840		in Buckingham E. and W. States II 117: ‘Prime Havannas’ [...] are only dealt out to his ‘silk-stocking and ruffle-shirt friends’ [DA].
1890		Music Hall & Theatre Rev. 133: Gus was very glad to be driving [. . .] to the Crenshaw area which was the ‘silk stocking’ part of University Division, where large numbers of whites still resided.
1891		Century Mag. (N.Y.) 5630/1: Silk-stockings [...] were formally regarded as extravagant and reprehensible, and as worn by men were regarded as an indication of luxurious habits; hence, the silk-stocking gentry or element, the luxurious or wealthy class [DA].
1903		N.Y. Eve. Post 30 Oct. 2: Political conditions change even in the ‘silk stocking’ quarter—the middle reaches of Manhattan, between 14th Street and 96th Street [DA].
1906		U. Sinclair Jungle 339: It had been no ‘silk stocking’ audience.
1911		G. Bronson-Howard Enemy to Society 102: There’d a bin plenty of convictions if those silk-stocking guys from up town ’ud kept their hands off.
1927		F.M. Thrasher Gang 347: At the top are the professional criminals [...] the so called ‘silk-hat’ gangsters.
1933		‘Paul Cain’ Fast One (1936) 234: MacAlmon - that’s Bellman’s silk-sock ward heeler.
1948		Time 5 July 20/2: In as chairman [...] went 47-year-old Hugh Scott Jr., a three-term Congressmen from a suburban Philadelphia ‘silk-stocking’ district [DA].
1949		Monteleone Criminal Sl. (rev. edn) 209: silk stocking bull A policeman working a wealthy district.
1981		McKee & Chisenhall Beale Black & Blue 14: [He] built an elaborate thirteen-room house just off Beale in a silk-stocking neighborhood where most of the residents were white.