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.