well off, especially in terms of happiness or wealth(from the notion of a well developed high cotton crop that one would not need to bend over to pick, used in the Southern U.S. since the 1920)
Meaning life is good or going well. Not intended to have any racial slur nor is it intended to be hurtful or racist in any way. As if to say things are going to work out and the crops are good so times are currently great.