from The American Heritage® Dictionary of the English Language, 4th Edition
- adj. Having plenty of money; prosperous.
from Wiktionary, Creative Commons Attribution/Share-Alike License
- adj. rich; affluent; prosperous
from WordNet 3.0 Copyright 2006 by Princeton University. All rights reserved.
- adj. in fortunate circumstances financially; moderately rich
From cock-fighting sense, a well-heeled cock was provided with sharp spurs and could inflict maximum damage. Then it came along in American frontier slang to mean that one was well-equipped. In the modern sense, however, it means being armed with the most powerful weapon: money. (Wiktionary)