Green’s Dictionary of Slang

(Aus./US black) aristocratic, smart, thus boastful, arrogant, showing off.

1871		H.B. Stowe Sam Lawson’s Oldtown Fireside Stories (1881) 31: He was one o’ these ’ere high-stepping, big-feeling fellers. [...] Drefful proud he was.
1899		F.E. Daniel Recollections of a Rebel Surgeon 247: Here am I—a fashionable high-stepping society swell, a tony physician, and a college professor.
1916		C.J. Dennis ‘A Gallant Gentleman’ in Moods of Ginger Mick 120: An’ Trent is one uv that ’igh-steppin’ crowd / That don’t sling praise around be ev’ry mail.
1923		H.C. Witwer Fighting Blood 240: He got his job on the strength of his acquaintance with the high-stepping bunch from college.
1935		The Mississippi Moaner (Isaiah Nettles) ‘It’s Cold In China Blues’ 🎵 She’s a high-steppin’ Mama.
1949		Monteleone Criminal Sl. (rev. edn) 117: high-stepping mama A female of easy morals; a lively woman; a prostitute.
1993		S. King Dolores Claiborne 9: No high-steppin kitty like Vera Kiss-My-Back-Cheeks Donovan.