It just needs to reach enough of a tipping point for companies to get behind it, and hopefully not be a fad that just burns out. This part is all very unlikely. The mainstream will have to get really bad.
To buy new "90s" stuff, it's not as good as what we had in the actual 90s. I watched something on new cassette players (walkman style) that companies are building. They are a lot bigger and bulkier than peak walkman, which was hardly larger than the tape. The tools and tech to make those small walkmans just doesn't exist anymore, and the market isn't large enough to invest in it.
When Apple's click wheel patent expires, I'm sure people would love to see some high quality 3rd party iPods that are easily repairable and have more modern features out of the box. There is still a community of people keeping the old ones going.
The way things are driving right now, it's going to be very hard to get a flip phone soon. My HSA plan just announced that if we don't download their app before fall they're going to lock us out of our accounts. That seems wrong in so many ways. In their FAQ there is a question about a user's phone not supporting their app, and the answer provided is to get a new phone that does. The HSA is through my employer, I can't just change, even though I'd like to. Earlier this year, before my grandma died, some company was telling my mom that my grandma needed an email address to use their service. She was 104 and months away from death, and they wanted her to get her first email account. After loudly refusing, they found away around it, but that's where we're at as a society. Can we even go back?