If you were to quiz people who preferred the Windows 2000 look, you would more likely get detailed answers regarding the design language and functionality. If you were to quiz people who preferred the XP look, you would more likely get answers revolving around colors and shiny.
Yeah, it was butt-ugly. The default Windows UI didn't actually look better until Windows 7, but I used the "Classic" look as long as it was supported. I skipped Windows 8/8.1 entirely, and while Windows 10 was reasonable in terms of how it worked, it was also butt-ugly, but now you couldn't do much of anything to customize it.
I don't understand why they couldn't have kept that option. The Windows UI is currently the least customizable I've ever seen and I started using Windows with 2.1.
That era ended 20+ years ago. Sorry, pal. Microsoft has been flailing since Windows 2000 to "improve" the UI, often with one bad idea after another: let's make Windows apps look like webpages, let's make Windows apps look like phones, let's remove all the graphics elements that let you distinguish one window or element from another, let's put 5 times more whitespace into every screen than is needed...
Yes, I can see where the Windows 2000 "Classic" UI was considered bland, but it was also the functional and consistent UI Microsoft ever made. Most changes since have been a step backwards.
Application developers often had a lot of crazy (and bad) ideas, but at least Windows itself was consistent. But then those crazy, bad ideas started affecting Microsoft, and then you could make the Windows Media Player look like eyeballs.
"Skinning" apps was a good idea in theory, but in practice, it never offered anything better than the default of Windows 2000 and earlier eras. Now you can't change anything in the Windows UI except a few colors.
I've been saying for many years that it seems most UI "designers" are just art school dropouts. Art school graduates would have a better sense of style, even if they weren't HCI experts.
Windows 2000 was peak Windows UI. Yeah, it wasn't visually exciting, but it was the peak of functional and discoverable UI. Of course, the Windows 10/11 UI isn't visually exciting either, and in many cases it's more boring looking, and definitely less functional. I would pay money to go back to the Windows 2000 UI, but I guess Microsoft isn't sophisticated enough to do that any more. The current Windows UI is less customizable than Windows 2. Yes, you heard me right. Windows 2.1 was more customizable than Windows 11.
Yeah, but I would still usually see Explorer crash within an hour of a fresh Win2k installation. Windows 2000 was peak UI, but it wasn't peak Windows. That was Windows 7. And Windows 7 was advanced enough that you could still go back to the Windows 2000 UI.
For people complaining that "Start" isn't a great choice, perhaps there's something better, but I can't think of anything. You need a small word that implies, "Click here to do something or find something." and in that regard, I think "Start" is a good choice.
On the other hand, I think there were few ideas worse than "My Computer", etc., not the least of which is the fact that it took Windows application software about 10 years to get consistently good at handling paths with spaces in their names.
Of course, the worst UI thing Microsoft ever did was hiding file extensions by default. That might be the worst UI decision in all of history.
I've witnessed this so much over the years. Much of the time when someone would ask me for help with something on the computer, I would have no idea, but I could discover the answer with a little bit of exploration and a good understanding of how UIs are supposed to work.
Windows 2000 was peak Windows UI, and everything since then has been worse.
Then Microsoft started thinking it was a good idea to make native applications look and work like webpages, which was a huge step backwards. Fortunately, that stupid idea didn't last too long, but it did have some lasting effects like the advent of "flat UI" style, but it was the beginning of the modern era of flailing around trying to improve on something that didn't need improving with one bad idea after another.
These days, I sometimes find that _I_ cannot figure some things out in software like Outlook or Teams that should be obvious because there are so many different styles of UI in these tools, many of which are not very intuitive or discoverable. Mixed metaphors, style over substance, and the idea that "flat" is anything but a way to turn your display into a sludge of rectangles of slightly different shades of grey with little or no differentiation between them, and few or no visual cues as to what elements of windows are clickable.
There are certainly things that are better now, like the popularity of "Dark Mode" which took about 30 years too long to happen, but in general, I don't think UI is better than it was 25 years ago, especially after Microsoft wasted 5 years or more on the absolutely misbegotten idea that computers should look like phones. Of course, the legacy is that Windows still has the remnants of about 5 different styles of UI in different places, and I wouldn't be surprised if there weren't a few Windows 3-era UI pieces still hanging around the Control Panel.
Windows 2000 was the peak of Windows UI. While features and functionality has improved in many ways, everything UI change since then has been a step backward.
Microsoft (and IBM and others) did a ton of good HCI research in the 70s and 80s, and used that research to make better UI for their operating systems. But sometime around the mid-90s when high-color displays started becoming the norm, UI experts started gradually being replaced by art-school types, and now it seems very little consideration is given to actual UI functionality, and the driver is entirely some bizarre sense of style from people who don't know anything about Human Computer Interaction, but seem to think no more deeply than "less is more".
These UI elements had reasons to look and act the way they did. This communicated information to the user (even if the user didn't realize it), and made software much more predictable and discoverable, and ultimately, more intuitive.