Green’s Dictionary of Slang

(US black) success; thus wear long shoes, to be successful.

[1968		N. Heard Howard Street 136: Anna Mae was nothing but an indolent whore [...] not worth the heels of a good pimp’s long shoes].
1968		N. Heard Howard Street 155: ‘What are long shoes?’ ‘Well, that’s more of an expression than a shoe. Y’see, long shoes are success. They’re the keen-toed design, right for kickin’ a whore in the behind when she comes up with short money or gits outta line [...] The ordinary cat, though, is satisfied just to show off the shoes and quote the high price of ’em [...] Just say that long shoes means the cat wearin’ them is into somethin’, or, if he ain’t an outright pimp, he’s doin’ good.’.