Ever since I started being more intentional about pursuing minimalism, I've thought that it's made sense to have fewer, but higher quality items. However, I've found that I'm that much more annoyed when something breaks, gets lost, is irreparable, shrinks in the wash, etc.
Yeah, stuff breaking and going out of repair is a fact of life, but I've found that when I spend more money on things, I get more upset when that happens. If my $12 sunglasses from Target get snapped in half, no problem! I'll just replace them - no sweat off my back. However, now that my $400 pair of glasses goes missing, I'm thinking, "why did I spend so much on those frames when I could have spent $100 or so?" (These glasses frames are only a year and a half old, mind you.)
Somehow if the high quality and/or expensive item has worn out and given me the years I expected out of it, I'm not upset by that...but rather, it's these cases where spending more money didn't necessarily buy me a longer-lasting item, or one that was all that much more well-designed.
There are a couple of areas that I've never struggled with, and have always wanted to keep my spending for quality to as minimum as possible: cars and technology. I don't get the bare minimum, but I get something reliable that I think will work for me in the long run. You won't see me buying the latest model cell phone or a luxury car...it's just not worth it to me to have that amount of money tied up into a depreciating asset.
The problem with clothes, shoes, and most accessories is that they aren't valuable enough to warrant an insurance policy, yet they break and go missing just like those higher-dollar items. Clearly I'm still balancing where I am on the continuum of spending $$$ to get quality....all I know is that I want to keep a minimalist lifestyle as much as possible.