Until Lynda inquired about the term well-heeled I had never considered the term hobnail. I knew that hobnails used to be hammered into the soles of boots to keep them from wearing down too fast, because many centuries ago when I was an army recruit we were issued with hobnailed boots. Or, rather, we were issued with the boots, and the hobnails, and told to get them hammered in quick smart, at the double, etc.
But why were hobnails so-called? Hob comes from hub, and hobnails have a large flat head a bit like a wheel hub. So there you are. Now, well-heeled (we are coming to it).
The reason the British Army insisted on our wearing hobnailed boots was to save money. They extended the life of leather-soled boots by, literally, years because the nails could be removed and replaced every few months. The boots, therefore, did not get "down at heel" as the leather wore away.
Of course only labourers and soldiers and similar lowlifes used hobnails. They weren't very practical for normal life, and so the constant repair of boots and shoes was a huge expense for most people. Those who were rich enough never to have to worry about being "down at heel" were "well-heeled". Simple.
The expression was first recorded in the United States in the 19th century. I can't give the original citation, but W. Beadle wrote in The Undeveloped West in 1873: 'To travel long out West, a man must be, in the local phrase, "well heeled".' A variant of down at heel was recorded in England in 1588 and it was common by 1700.
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