Boots theory is attractive because it's pretty obvious that more expensive products are nearly always better quality. But what actually matters is whether the increase in quality is greater than the increase in price, which I think is much less obvious.
There are plenty of answers to the question. But one approach is to make sure it looks as good and works as well for the return period, but doesn't last as long. E.g., you use less material, short the structure in favor of the surface, use lower-quality material, invest less in production quality, or offer shorter warranties.
For example, think of a raincoat. On one end of the spectrum we have the $0.99 disposable poncho, which is basically a garbage bag with a different cut. Up from there are all sorts of methods of improvement: https://www.rei.com/learn/expert-advice/rainwear.html
The better raincoats tend to be correlated with price because if a feature doesn't require additional expense, low-end manufacturers will just add it. And also because while many consumers aren't discerning about quality, many are, and will pay extra for it. Places like Wirecutter and Consumer Reports do the sort of testing that helps keep people honest.
That said, you're very right that there are many other things that influence price. A Burberry raincoat will be 10x the price of REI's favorite raincoats, but it won't last 10x as long. So Boots Theory, which is about good pairs of boots being more expensive than shoddy ones, is correct. But you can't work it the other way and claim that expensive things are always good in the way a night watchman thinks about his work boots.
I have a pair of dress shoes that are approaching ten years old. I spent more than I ever had on any pair of shoes but they continue to be comfortable and are easy enough to resole, clean, etc.
There are enough items in the world of apparel (I hesitate to use the word "fashion") that are timeless, at least on the scale of a human lifetime. My belt is twenty years old. My watch (due for service) is over twenty years old.
A good shirt will last longer than a cheap shirt. If you buy carefully (i.e. not just what's in "fashion" that season), it can work for a long time.
I had a US-made dress shirt that lasted me close to 15 years and I think I spent less than $40 on it. It's a shame those mills are long gone because few shirts last that long and I'm not willing to find out if spending $400 on a shirt gets me the same quality.
At some point clothes become a Veblen good. The idea is to spend on quality, not on marketing or details that don't add to the durability of the item.
While this is possible, I don't think that's really something you can go about with your life. Shit luck does happen. But you can keep your boots away from your dog.
You should acknowledge black swans, but you shouldn't plan your entire life around accounting for them.
So what's my probability of moving to a beach town and never needing boots again? Probably very low, since I will be unlikely to move and even if I did I would still use my boots for things like hiking, working around the house, etc. The risk is therefore very small as well. The same can be applied to your other scenarios. Uncertainty makes us uncomfortable, but it can often be reasonably quantified.
If my laptop, tablet, Garmin GPS or phone break, I am inconvenienced. As opposed to, completely dead in the water.
