Oh hey I'm uniquely positioned to answer this; though I'm in tech (and at this point frankly speaking well-compensated) my family have been bootmakers for decades.
I'm sitting at a tech office right now wearing a pair of boots that my father made for me in 2015 - regardless, they're absolutely spotless and I'd wear them to a formal event without hesitation. Every 6 months or so when I'm by his store I shine them up and put in a fresh pair of leather laces. Every 3 or so years, he re-soles them when the soles eventually wear out and lose traction. Eventually they'll require a rebuild, but they've got probably another 5-10 years of daily wear in them before that. I've got a few more pairs I swap between every so often, like a pair with OD green canvas that looks nice with khakis, but these solid black ones are my daily wear.
While 10 years sounds like a good run for boots, my father has a pair at ~35 years old now that he still wears frequently. IIRC they've been through one or two rebuilds and few re-soles in that time.
Were these commodity sneakers, I'd be purchasing a new pair every few months. Even nice running or trail shoes only tend to last a few hundred miles in my experience, but I've put tens of thousands on these and will get ten thousand more easily. Re-soles and rebuilds aren't free, but they're less than a replacement and put years of lifetime back on the boot. They're also comfortable as hell and fit me like a glove.
So in short: yeah, rich men do wear the same pair of boots for 10 years, or even far longer.
Not all boots are made the same though. I had some bad luck with a pair of veldtschoen welted boots from the English firm Crockett and Jones in a custom leather. The commando sole split twice at the toe, which they repaired, but after less than five years of wear the lining at the heel had worn through.
I took them in to be rebuilt, but after inspection they said the stiffener had come loose, and nothing could be done. Here have your expensive and now broken boots back.
I'd assumed when I got them I'd be wearing them for decades, and at least a few rebuilds. Maybe there was something wrong with that specific pair, but I did have a goodyear welted sole randomly detach from a pair of six month old city shoes from the same firm. And yes I had been looking after my shoes (frequent cleaning and polishing, always using shoe trees, skipping days between wears, etc).
When I had a pair of Church's fall apart I put that down to them no-longer being a quality brand, but now I don't think you can guarantee a long life just as the shoe was expensive and from a reputable brand. I have many shoes that have lasted better (and now since covid I don't wear polished shoes daily), but that does sometimes feel like luck of the draw.
Yes, that's my family's business, I'm glad to hear you've had such great experiences. Similar to you, I've never looked back; every time I put on trail shoes I yearn for my boots again.
Purely anecdotal, but I know friends have used Nicks without issue. The basic advice I got was to buy jackets and leatherware from places in Washington and Oregon.
I'm sitting at a tech office right now wearing a pair of boots that my father made for me in 2015 - regardless, they're absolutely spotless and I'd wear them to a formal event without hesitation. Every 6 months or so when I'm by his store I shine them up and put in a fresh pair of leather laces. Every 3 or so years, he re-soles them when the soles eventually wear out and lose traction. Eventually they'll require a rebuild, but they've got probably another 5-10 years of daily wear in them before that. I've got a few more pairs I swap between every so often, like a pair with OD green canvas that looks nice with khakis, but these solid black ones are my daily wear.
While 10 years sounds like a good run for boots, my father has a pair at ~35 years old now that he still wears frequently. IIRC they've been through one or two rebuilds and few re-soles in that time.
Were these commodity sneakers, I'd be purchasing a new pair every few months. Even nice running or trail shoes only tend to last a few hundred miles in my experience, but I've put tens of thousands on these and will get ten thousand more easily. Re-soles and rebuilds aren't free, but they're less than a replacement and put years of lifetime back on the boot. They're also comfortable as hell and fit me like a glove.
So in short: yeah, rich men do wear the same pair of boots for 10 years, or even far longer.