Why do we say that someone with money is well heeled? The Answer: To be down at the heels is to be in bad financial shape. The worn-away condition of the bottom of one's shoes reflects a diminished bottom line. So being well heeled would present the reverse situation. Right? Wrong. The heel in "well-heeled" originally belonged to a gamecock, a bird trained to fight other birds to the death while men wagered on the outcome. A bird's owner would attach a sharp spur to its leg to make it deadlier in the cockfighting pit. The fowl was then said to be "well-heeled." In the western United States in the 19th century, in the same spirit, this expression was applied to men who were well armed. Ultimately being well heeled carried over to the financial realm, where it meant that one was financially armed to better deal with life. Think about all this if being well heeled makes you feel cocky. (Source: HEAVENS TO BETSY! By Charles Earle Funk)