I will bluster, but I don't deeply care that my 80-90 year old style is opaque to a lot of people. It's a bit sad, because ignorance here strips away a layer of meaning whenever you engage with art/history in or about this era.
What's more disconcerting is the thought that folks are just consuming clothing without thought or purpose, including what goes into their own closet. That leads to a lot of waste, and a lot of insecurity when you can't figure out why your clothes don't make you as happy as that Influencer.
I don't know how we get fashion literacy back -- fast fashion and trends cycling seasonally vs every so many years is to blame, imo.
When I talk about what appeals to me w/my own style, I get loads of "wait, clothing communicates things?" comments, which is an interesting commentary on how we now consume fashion with little thought, other than "current trend".
Not enough people these days seem to be involved in subcultures (or are aware that they are in one). And that contributes more to the loss of fashion vocabulary than, say, not following someone like menswear guy.
I guarantee you are dressing to communicate something to other people, even if you're not fully aware of the fact. Your clothing will continue to communicate *something* even as old trends compress. Fashion can be art, it can reflect the zeitgeist of a time period, and it can be propaganda.
If your clothing is making you unhappy, but you can't figure out why:
This isn't a vintage vs modern thing. It's a "clothes have meaning" thing, and I encourage folks to step back and think about what clothing is saying. Look at everyday people, celebs, movie characters. From the old-timey weirdos like me, to the $300 tailored t-shirts of the tech bros, there's a lot going on under the hood. And the more you know, the more confident you become about your own wardrobe and less prone you are to chasing trends that end up disappointing you.
I really encourage folks to embrace "slow fashion". Not just as an anti-capitalism thing, but as a way to examine how you want to present yourself to the world. See what the fashion you share (or want to share) with others communicates. And see what your own personal style that sits atop that says specifically about you.