That said, I think there is a correlation between the amount of social signalling one must do to be successful in a society and the amount of wealth that that society allocates to those that are capable of navigating organizations. It's one of the reasons I think the tech sector is mostly jeans and sneakers.
Fancy shoes don't mean you're capable of knowing what a gin index is or when to use it.
While I have many qualms with modern tech, this is not one of them.
Ideally your rain jacket is appropriate for weeks-long alpine or warmer-weather arctic expeditions, and costs at least $250. It should pack down unbelievably small so you can excuse/brag-about the expense as an expression of "minimalism". You wear it on your $1000 bike for your 2km commute to the coffee shop to work on your MacBook. Shoes should be ready for many kilometers of hard, high-performance trail running, and should have been priced to match. Or else rock climbing or bouldering. No activity is more hip-tech-culture-approved and laudable than rock climbing, at least for now (the trends come and go).
There's that stuff, then there's the hipster-mimicking tech-fashion sect in $200 Japanese selvedge jeans and $300ish Red Wing Heritage workboots. There's plenty of overlap and mixing of the styles, though.
Don't forget the right hoodie. If the aglets aren't metal and the zipper's not a heavy, smooth-but-crunchy-feeling YKK, you've screwed up.
If in doubt, just shop REI and Patagonia. Little they stock will be too far off the mark.
For instance it is an old people’s saying in Japan to look at someone’s shoes to know if they are rich/value good objects (the basis of that was that poor/undiscerning people would have poor shoes maintenance, or plain bad shoes).
Or you would tell someone’s rank in a company by the amount of stuff he (was about men, yes) was carrying every morning (basis was higher ranked people would have less manual roles)
Of course these saying become pointless and people find other stupid stuff to look at to rank other people on a scale. But yeah, in my short experience it’s a thing people train to do, and is valued as useful skill.
Also as people tend to dress rather uniformly, so you need a decent amount of effort to stand out without being flashy, which means trying to prove good taste with exotic and expensive but plain looking goods, that you justify owning by touting their good quality and not their high price.