In these days one is well heeled who has plenty of money, is well fixed or well-to-do, just the opposite of one who is down at the heels.
Since the latter, down at the heels, alludes directly to the usual run-down condition of the shoeheels of one who is hard-pressed for money, it might be supposed that well heeled originally alluded to the reverse condition.
But that is not the case.
Originally, back in the eighteenth century, it was a game cock that was well heeled; that is, provided with a good “heel” or artificial spur before it faced an opponent in the pit.
From that, in the United States, men began to “heel” themselves, to arm themselves with gun or pistol, before entering a zone in which trouble might be expected.
If well armed, they were “well heeled,” from the troubled days in the West, and in the South following the War between the States.
Hence, perhaps because most troubles can be alleviated by money, the expression soon took on its present financial aspect.