Green’s Dictionary of Slang

1. of clothes, unfashionable, worn-out.

1850

Fast Man 6:1 n.p.: ‘D—n it, Ned, how you stares at a cove. I suppose it’s because my toggery’s rather shakey. What game are you up to that you’re such a swell.’ Sam Evans, that was this fellow's name [was] dreadfully queer dressed; his hair was prison cropped.

2. (US Und.) of a town or city, unsafe for criminal operations; similarly of a place targeted for a robbery.

1940		D. Maurer Big Con 226: If the town is ‘shaky’ – that is, if the fix is not very strong.
1969		‘Iceberg Slim’ Pimp 264: I had her several months when the town got shaky.
1997		E. Little Another Day in Paradise 136: If the residential shit is shaky, we’ll take a pass.