My weight fluctuates, my clothing needs change, my style changes, I discover a new type of clothing item that obsoletes an old one. Or stuff shrinks, rips, gets stained, gets lost.

Expensive "long lasting" clothing isn't usually worth the investment in my experience for all of these reasons.

Outdoorsy equipment may be an exception, but I don't feel like it's the case for regular clothing or merchandise in general.

(Plus a lot of expensive stuff isn't actually any better quality than the cheap stuff, and it takes a lot of research to figure out when the expensive stuff actually is worth it and when it's not.)

A cheap jacket for $50 dollars or a (well researched) jacket for $150 is an obvious win. Warmer, more durable, more comfortable, and looks better. I bet it can last 3 times longer than the cheaper jacket in a lot of cases, plus it could probably resell for much more. We don't often talk about equity in smaller purchases (probably because it's not as consequential), but buying good items means they'll probably hold value better for resale (same goes with buying them used).

And it's worth it - I've had two pairs (from ebay) that have lasted me for 10 years between them. Resoled many times, but still absolutely excellent.

10 years!