You can certainly buy shoes that will last for decades, if you're diligent with maintenance. BUT, you're still going to need (probably) multiple resoles, patch

You can certainly buy shoes that will last for decades, if you're diligent with maintenance. BUT, you're still going to need (probably) multiple resoles, patching, and what not. Take a look at the shoes Prince Charles is wearing - they're bespoke shoes from the 50s. But you need to ask yourself - at what point do you just scrap them, and buy a new pair? Some people love the vintage "relic" look - but every resole and patching is going to cost you money. Purchasing a pair of $1000 shoes, and then spending $1000-$2000 on maintenance the next 50 years will make sense for some, but not for others. I personally, would much rather just buy a new pair of $500-$1000 shoes every 10-15 years, and discard the old ones when they start to look too shabby. I live my guitars old and reliced, but shoes ? No thanks. When / if my shoes need patching, I'm throwing them.