Good foot wear is one of the keys to avoiding chronic pain when you walk, hike, or just stand a lot. Your buddy obviously does none of those things on a regular basis, or he would know.
Working in the woods for a career taught me this lesson when I was 24 years old. If you go cheap on your gear, you will wear it out faster and replace it sooner. A sale on a quality item is a good value if it performs well. A sale on a cheap piece of junk that will be ruined quickly is not a good value. It's just throwing less money away than if you'd paid full price, but in the end, you may have still spent your hard earned money on garbage. Old Dog mentioned boots. I'll mention active gear as well.
The first time you go cheap on boots when you work in the woods, and you have a rain shower come through and completely soak you at 9:00 in the morning, and then you realize you have to work until 5:00 pm, is the last time you ever go cheap on boots.
And they are wrong on 95% or more of products out there.
I will never buy a Rolex unless I fall ass backwards into money, but I will never fault anyone who chooses to buy quality, so long as it's real quality and not just a name. But even if they choose to spend their money on a name, it's their money, so I don't really care.
It's only showing off if you are intentionally showcasing what you have with the intent of evoking envy. For that reason, I've never really understood the phrase "pride of ownership". What does that mean exactly? I save money to buy what I want because it will facilitate an activity. It doesn't evoke pride. Saving money is something any adult with a decent job and life circumstances should be able to do. It's a life skill. Spending money is just spending money. I take pride in my accomplishments, not in material goods I own. It's just stuff. Stuff that helps me do what I want.
That being said, I want my stuff to last a long time. So I try to take care of it.