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I wear my shoes to death. But I have a pair of Footprints by Birkenstock black loafers that I've worn for 6 years. These are good German shoes, and they have performed well for me. They are good to go for next year too. I do believe than can be resoled. I have an even older pair of Footprints--clogs--that are even older, but I haven't worn them as often as I have the loafers.
I have a pair of Aravons, which I had customized for my feet that I have been wearing for what seems like forever, but I think it has only been 5 or 6 years. I do want to kick those to the curb. They don't feel as good on my feet as they did a couple of years ago.
I forgot about a pair of blue suede clogs by Born. My gosh, I've been wearing those for over ten years now. They absolutely will not die. They look great with jeans. And I've literally never done a thing to them, not even polished them.
I have a pair of heavy black leather sixteen inch boots with a wood stacked heel that I bought at Berman's in 1983 that are still in good shape. My feet are not as narrow now as then so when I took them to the shoe repair shop to have zippers put in the sides the cobbler said, "You never see boots made as well as these anymore." Paid what seemed like a small fortune for them in those days - $80.00!
Also a pair of Harley black leather hiking style riding boots that are thirty years old and show little wear.
I have tons of shoes that are ancient, but have hardly been warn. I've had two instances where I've worn an old pair of shoes and the soles have fallen off, or disintegrated, halfway through the day. The strange part is that both times we were with the same visitors, who come about once a year.
One pair, I know I had before 2004. It was an awesome pair of Born clogs. They looked as if the soles were stitched on, but they were only glued on. The other was a pair of Rockports that were probably that old too. The rubber soles disintegrated.
I have a pair of ancient UGG boots that I never wear now, because I live in a warm climate. I'll always keep them, but I hope when I wear them again the soles don't fall off.
I have several pairs of Frye boots that I've worn for twenty plus years. Had them resoled and I take great care of them - they still look almost new.
Oldest pair of shoes I own and still wear are classic Doc Martens - lug sole, flat black with contrast stitch. So comfortable, so easy. I think I got them when I was 19. So almost 25 years now.
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