Don't know what I'd answer you if you asked me what would constitute a worth in a leather jacket to me right now. Yep, a pricier leather jacket does look nice(r) but at this point, I can't imagine what would make it so different that would make me feel like paying an additional grand was so totally worth it and I'm saying that after I've just wasted near $2000 on a jacket a few months ago. I don't feel too good about it, to be honest and it's the last one I'll ever pay full price for. Not paying those prices either ever again.
I don't really know what I want anymore, I guess... I guess I'd really like a Memphis jacket, though. That's the one I'd pay money for. Maybe I should sell the LW and get that one instead.
But I can't really say what's this clothes business done for me anyway... Maybe that's the whole reason I feel this way. Collecting suck. We feel getting that certain something will change our lives in some way and it doesn't. Doesn't really matter at all and doesn't change a thing. Just time and money wasted. You are right. It's better not to own much - or anything.
I reckon a few things that you really love and the rest of your clothing 'working/functional/socialising' is fine - you have to have things that you enjoy, after all. Money wasted isn't catastrophic if it teaches you to conserve it (or to spend it on things you really enjoy), and there's no help in being your own worst critic for too long a time- consumption (and conspicuous wastage) is what most people are taught should make them happy. For some people it does and for others it highlights a lack of some kind. I stopped buying as much stuff when I started reading again (when I say reading, I mean I'd pick three novels and that'd be the objective for the next week or ten days' evening reading- the best part was that after a while doing that, I'd lost the research/buy habit and I could pick up and put down a book like most normal people).