Green’s Dictionary of Slang

high cotton n.

also tall cotton
[the wealth that comes from a high cotton crop]

(orig. US black) the good life, the materially successful life.

[US]C.H. Hogan ‘A Yankee ... on Texas Speech’ in AS XX:2 Apr. 83: That fellah sure thought he was in high cotton.
[US]P. Conroy Great Santini (1977) 426: We accidently stepped into high cotton back there. This is a real chance to pick up a little cash dough.
[US]J. Wambaugh Secrets of Harry Bright (1986) 217: This is pretty tall cotton for a guy that used to work the streets around Southern substation.
[US]T. Willocks Green River Rising 255: If you can learn to live right in here [i.e.prison], back out in the world you walkin’ in high cotton.

In phrases

shit in high cotton (v.) (also shit in tall cotton)

(US) to live prosperously, to feel happy, to be important; euph. alternatives include fly in high cotton, live in high cotton, travel in high cotton.

[US]Wentworth & Flexner DAS.
[US]E. Bunker No Beast So Fierce 130: We’ll be shittin’ in tall cotton soon as I make a score.
[US]E. Bunker Animal Factory 119: I stayed out four years last time, stealing every day. I shit in tall cotton the whole four years.
[US]Maledicta IX 160: They have not adopted U. S. city nigger use of country nigger expressions such as shit in high cotton.
[US]S. Morgan Homeboy 26: ‘Shittin in tall cotton,’ was the style to which the Woppa [...] was accustomed.
[US]E. Little Another Day in Paradise 46: Alarm’s a piece of cake, you’re in, and we’re shitting in tall cotton.
[US]D.R. Pollock ‘Giganthomachy’ in Knockemstiff 63: [C]ompared to what William and his sister, Lucy, had to go through, I was [...] shittin’ in high cotton.
[US]S.A. Crosby Razorblade Tears 272: ‘We still staying in that hotel. It’s pretty fancy. Like you would say, “it’s like shitting in high cotton”’.