I don't know what you're arguing against here.
More expensive stuff definitely lasts longer, in general.
> $30 shoes from DSW
These shoes aren't cheap, they are what is called "seconds." They have design flaws. I buy shoes from DSW because they are $300 shoes for $60 because they are missing a stitch. They are still technically $300 shoes...
> Our clothes from Sears lasted forever.
That's fine, but Sears is mid-ranged. If you buy something from Walmart it's going to lose the wear-ability very quickly. Maybe a polo would be fine, but a Jacket, pair of shoes, or pants will not hold up like something a few times more expensive will.
> Middle class people don't sigh in relief about being able to afford hipster boots, they just buy the same sneakers they always did.
Middle class people generally buy $100-$200 Nikes.
> My fancier clothing wears out faster, my more complex lifestyle means more handymen and repairs, etc.
??? What? What are you buying, exactly?
> Its really not. When we were poor we just didn't buy into the consumerist lifestyle. We just kept stuff forever.
Very-cheap end things don't last as well as mid-ranged things do. It's a fact. You won't be buying new TVs, but the consumables you buy suck: watches, jackets, the food, your cars, dishes, forks and knives, computers (for work), so on... which leads to you purchasing them more often.
It doesn't mean the HIGHEST END stuff is much better. You have diminishing returns. But, it's very tempting to buy the CHEAPEST when you are poor.