Green’s Dictionary of Slang

booted adj.1

[boot v.4 ; Willie Bryant’s ety. in Jive in Hi-Fi (1958) is spurious; note Burley, Original Handbook of Harlem Jive (1944): ‘The fellow who is “hipped” or “hepped” is common indeed. But the one who is “booted” is a unique individual [...] To be hipped one has to have his boots on. The tighter the boots are laced, the more hipped the wearer is supposed to be’]

(US black) aware, knowledgeable, smart.

Show quotations
D. Burley N.Y. Amsterdam Star-News 22 May 11: Hip-cats who are booted to the play.
[US]Down Beat 28 Jan. 6: Another ‘booted’ character on WJLB’s assembly line of jockeys is Phil McClain who spins an all-night record show.
[US]W. Bryant Jive in Hi-Fi 13: It [i.e. booted] comes from the story of a fisherman warning young fishermen never to wade in deep water without hip boots because they could run into trouble. So, when you hear the words, ‘I’m hip’ or ‘I’m booted’ it’s said to let you know they have no fear of trouble or that they understand what’s shaking.
[US]T.M. Kochman ‘The Kinetic Element in Black Idiom’ in Kochman Rappin’ and Stylin’ Out 169: It can mean being knowledgeable, aware, etc., as in the expression, ‘I’m booted’.