Green’s Dictionary of Slang

1. a sophisticated, urbane pimp or swindler.

1974		Piñero Short Eyes 125: Longshoe Someone who’s hip, slick, and ‘has his act together’ [HDAS].
1980		A. Pearl Dict. Popular Sl. 93: Longshoe n. A self-confident, urbane person [HDAS].
2005		K.E. Campbell Gettin’ Our Groove On 67: Long-Shoe Sam is definitely an exemplary blend of the trickster (or pimp) and gangsta.

2. as long-shoe game, the profession and lifestyle of pimping.

a.1958		‘Broadway Sam’ in D. Wepman et al. Life (1976) 96: He lived off the hicks from out in the sticks. / He was a master of the long-shoe game.
a.1964		‘Honky-Tonk Bud’ in D. Wepman et al. Life (1976) 58: He looked real square but was everywhere, / A master of the long-shoe game.