Originally Posted by BBC
In the US, those kind of shoes are traditionally called "the Boston cracked shoe" look - one should be impeccably dressed, except for shoes that look like they're long past their useful life - it's obviously a not so subtle hint that although the wearer is wealthy, he admires well-worn traditional things and is frugal.
Here's a pair of Cleverlys that were in heavy rotation for 40 years - follow the link for a larger version of the picture (http://3.bp.blogspot.com/-8R-QRniy7l...Cleverleys.jpg
So Alan Flusser says in Style and the Man, but he also points out that it's a look and a set of values that have passed into mid-20th c. history. Personally, I love very old things, be it furniture, or well cared-for shoes. But you can only get away with this particular look in specific circumstances. Prince Charles can wear them, but a member of his staff never could.
However, I have noticed an interesting thing. I have an old Barbour jacket which I wore most days this past winter. It is showing its age, in terms of patina, shall we say, and has a few small holes here and there. People stop me and ask about it. One of them, a stranger, said that at the Barbour shop on Madison avenue they sell vintage ones just like mine for more than the price of a new one. So... maybe we are entering a new era where the appreciation of good things that are kept and worn to shreds will return. As for my oldest shoes... I'm not throwing them away.