I'm going to draw on interior design wisdom from William Morris here. "Have nothing in your houses that you do not know to be useful or believe to be beautiful." It's not a bad rule for deciding when to buy a high-end item over a lower-end one.

If you know you'll wear it to death over multiple seasons/years (perfect black boots, a great winter coat, the exactly right bra), it meets the "useful" criterion and is worth a high price tag. If you find it so stunning that it brings you great joy, it meets the "beautiful" criterion and *might* be worth a high price.

I say "might" because I think it's important to be careful here. You can end up with expensive orphans. Because I don't trust myself in this regard, I stick with the useful workhorse criterion. I'll spend more if something is high quality, hard to find, and will get worn a ton. Right now for me, that's good shoes. But I won't spend a lot on certain workhorses that I tend to lose, such as winter gloves or pearl stud earrings. Even if I wear it every day, I won't pay a lot for something that's likely to be left in a taxi.