I think a lot of us came of age during that time, and as such see it as the ultimate UI.
[EDIT] The move away from native toolkits and to very-custom UI for everything is also plainly bad. Java and Flash got the ball rolling on that (and both rightly caught shit for it) but Webtech junk is what really made that awful pattern take off. "Corporate really wants to make sure our checkbox elements are on-brand" OH MY GOD what an incredible waste of money, when you consider the total cost to the industry as a whole, in order to make UIs worse.
I'm half-joking. I know what you mean, but I think a larger picture is that touch-interfaces have their own problems/solutions that the traditional Desktop doesn't have, and vice versa. I think that the desire to have One-Interface-To-Rule-Them-All leaves a lot of people (and possibilities) behind.
It would be a lot of work, but I think Microsoft needs two entirely separate Desktop Environments. One for touch-based devices, one for Desktop. I'm not holding my breath, we've been debating this since Windows 8. And I'm fully aware that as a middle-aged Windows Application developer that my opinion matters less with every year that passes... but I can't help but feel that maybe we've thrown the baby out with the bathwater.
It came as quite an eye-opener to me recently to realise younger people now entering the workforce view the mouse as an archaic input device.
I was looking at Reddit the other day, on one of those r/flippingamazing type subs, and someone posted a picture of a disassembled mechanical mouse, to show off the wonders of 1900s engineering. I tell you I nearly spat out my false teeth. Had to take a Geritol to calm myself down.
(* They're more correctly called opto-mechanical since the movement sensing is done by way of a slotted disc interrupting light beams.)
While some people might see Win95 as a good GUI because that is what they first learned, that doesn't mean that applies to everyone. And if nothing else it also works the other way around - "kids these days" may not mind navigating around flat touch-based interfaces because they've spent the time to learn them, not because of any inherent superiority of said interfaces.
This is why IMO using how easy kids can use/learn something (in computers at least), be it UIs, languages or whatever isn't very helpful - kids have a ton of time and if they like something they can spend ages on it regardless of any inherent properties of that something. I mean, consider the downright atrocious UX the overwhelming majority of games had in home computers from the 80s and PCs until early 90s - and yet kids at the time spent hours deciphering and playing them. That didn't mean the games actually had good UIs, it meant kids had enough time and motivation to work around these UIs so they can enjoy the games.