I'm 23 and IMO, the Windows desktop style leaked somewhere in Windows 95-2000. The first Windows I ever used was XP, so I'm mostly making that decision based off screenshots and emulators.

UIs back then were dense, didn't waste large amounts of space in a misguided attempt to be "minimalist", and had affordances for ease of use. There was no scrollbar hiding, no animations that made the user wait for no reason other than the designer's ego, very visible borders on windows and buttons that made finding/resizing them easier, large bars at the top of windows that let you move them around, and actual text for most buttons instead of icons that are anyone's guess what they mean. Thankfully some of this can be dialed back in the Windows 11 accessibility settings, at least for missing scrollbars and getting rid of time wasting animations, but a lot of programs don't respect those.

That's right there is a good indicator for which programs care about their users. I'm using your program because I want to actually do something, not waste time watching your designers show off.

I've disabled animations on my Android phone too, and it gives an extremely noticable speedup. Menus appear right when I click them, instead of a second later as they slide into existence. Too bad iPhones just replace the slide with a fade of equal duration; disrespect for the user's time like that is yet another reason I will never buy one.

Those older GUIs didn't try to hide the filesystem hierarchy either. It infuriates me to no end when I use a new OS and have to hunt down the way to show the disk root, or filename extensions, or hidden files. MacOS was especially bad; I had to look up a freaking keyboard shortcut that I never would have found on my own. The common reason is so "normal people" can use the interfaces, but I think that's infantilizing and is why tons of Gen Z don't know what files or folders are. Most people can learn .docx means a Word document, and C:\Users\TheirName is where their files are.

(Notable shoutout, the GNOME open/save dialogs are the absolute worst. I wish distros wouldn't default to it. People will just go right back to Windows 11 because it's somehow better.)

There's some improvements possible, for sure. I'd like to see some programs put hint letters over buttons when you press a modifier like Ctrl so you can easily see what the shortcuts are. I don't know of any that do, but it'd be very useful for more complex software like drawing programs or word processors.

For some of these, you have to use them on the actual hardware to understand why so many of us are bummed about what we have lost. The latency of modern systems is kind of bonkers. Even though the machines were incredibly slow they feel faster than modern machines. Some musicians used Atari STs for years after they were discontinued because of the stable timing.

For others, the hardware wasn't important, but some of the functionality isn't apparent in a static screenshot. For example, I loved OS/2 and the Workplace Shell. It had functionality similar to Windows COM or CORBA in that everything on the system exposed an interface that could be easily scripted or used by other applications. The built-in scripting language was Rexx which I feel could have played the role Python does now if only OS/2 had taken off. Using OS/2 from 1.3 onwards felt like you were using a computer from the future.

There is definitely an element of nostalgia. However, a lot of earlier desktop OS GUIs do seem to be more internally consistent and with more emphasis on usability than the current crop. I think part of the issue is that things that might make sense on a phone have bled into desktop OSes, where they make a lot less sense.

Basing one's opinion on how a static screenshot looks, is the reason we've moved towards pretty looks and away from usability concerns.

As other commentors have said, the overriding concern with these older OSs was to make them as easy as possible to use. It would never have crossed these developers' minds to, for example, hide the scrollbar because they think it looks ugly.

Looking at a screenshot doesn't really tell you anything if you're not familiar with it, but it's a nice reminder of using that software for those who are.

In most of the comments here, I'm not seeing "nostalgia" or "the love for youth". I'm seeing frustration with how the carefully researched and developed principles have been forgotten.