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Windows 1 had hamburger menus, originally from Xerox Star.

Kinda cool

I cannot accept this slander of Windows XP.
I started using keyboard navigation more and more around Win 7 and that has actually improved quite consistently since then and I remember Win 8 Win-key search was quite good, if you could look past the start menu…

Also reminds me of the layers of UI versions still present in Windows https://news.ycombinator.com/item?id=27556754

8 for Windows 11? An OS that includes ads in the Start menu, made with React. I'm not even mentioning right-click, which has basically two views: you open it and see some uselessly chosen tools, and you still need to open the old version (with the old design, breaking design consistency) to access actually useful things. Viva Windows XP!
To me personally, it feels like Windows 2000 was the last and maybe only consistent UI onto which all later versions bolted what they considered improvements without ever overhauling the UI in full.
Windows 11 < Windows 10?

Just based on the start menu alone I can‘t think of any reason for 11 to lead the ranking

11 is indeed pretty good looking. Once you use it 10 feels so clunky.
I assume there is a reason for leaving out Windows Me.
As someone who grew up with Vista (yeah, I'm young) I will always love that look. Probably a good bit of nostalgia, but as a kid who couldn't really even manage files well that always looked so fancy and fun!

Even still have the laptop I used back then, fully with the barely functioning charging port that makes booting it up an exercise in dexterity.

> With Windows 95, Microsoft managed to produce a version of its OS that scared Apple so much they ended up bringing Steve Jobs back, along with his own operating system, NeXTSTEP

Funny because Windows 95 contains many ideas from the more ambitious project codenamed Windows Cairo that was intended to mimic NextSTEP. Cairo was never released, but the gray slab 3D look, the "X" button on the top-right corner on Windows 95 are the hallmarks of NextSTEP.

Windows 95's most original GUI idea was the Start menu.

I think Windows XP should have shipped with the Watercolor theme, although Luna does a better job of setting it apart from previous versions
Give the Windows 2 a second look and try to ignore the colorful GAME in the screenshot.

It’s actually pretty ”elegant” design with white, black, grey with two shades of primary color: dark blue and light blue/cyan. Then complementary orange for active selection. The cyan is light enough for black text and blue is dark enough for white text. Really good palette choices.

Remember this was only 16 CGA colors, of which only few are delicate enough for UI components.

The tiny resolution makes things blocky, but if it had more space with an SVGA resolution, it’d be pretty great.

I would dare say, this might be the most ”designed” UI of the bunch, considering limitations.

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Intresting aspect of the UI is the hilighting of the menu bar in each window:

These days it’s odd to hilight menus, but I think their importance must’ve been much higher due to lack of space in the UI itself. They were basiclly act as ”navigation” and action menus. We use sidepanels and tabs a lot, but those have hard time fittinh there. Also the apps were simpler.

I still consider Windows 2000's UI to be the peak of computer interfaces and nothing else has come close to its effectiveness and clarity for day to day work.
> I still consider Windows 2000's UI to be the peak of computer interfaces

Only on Windows.

In hindsight, I really love the way Vista looks. I don't think I ever used it as a daily driver (I went from the family XP computer to a Win7 laptop, I think), but the glassy transparency is certainly something.
I like the “did it improve or regress” angle.

I hope it’s not controversial if I say that in the Apple world, Liquid Glass is, if not the first, certainly the worst regression. And I think this could have been predicted if you agreee with OP about Vista.

I'm surprised nobody caught this, but both the screenshot for Windows 8.1 is not Windows 8.1, it's Windows Threshold, the development phase of Windows 10.

The specific screenshot they show is the very first start menu they cobbled together for Threshold, which would later be redesigned again before shipping as Windows 10. The screenshot is also showing off early adaptations of Windows 8 apps running in movable windows -- before that, they could only run full- or split-screen!

I remember hacking the "Start" button in 95 through 7 to say "Whee!" instead of "Start". Childish and silly, but I liked it. I miss being able to make little hacks like that.
Haha, I totally forgot about that. Pretty sure mine said "Win95"/"Win98".

Sadly though, this kind of hacks doesn't satisfy me the same way it did 30 years ago, when I had all the time in the world to tinker.

It's the same story with things you can customize, today I rarely bother spending more than a few seconds on clicking around to choose the next best thing.

remember that there are still classic theme bois out there. 9x/2k is the best theme.
I really hated the depressing grey GUI of Windows 95/98/NT/2000/Me. It looks like working in a dull grey concrete office with a grey PC and grey monitor while wearing a grey tie. I get that Windows XP and 8 look too colorful for many people (I like them), but Vista & Co, with their glass design, managed to avoid colors while still not making everything a drab grey.
They say "I am skipping over all versions of Windows NT" and then proceed to rate XP, Vista, 7, 8, 8.1, 10 and 11.

* Also 2000, but at least they seemed to be aware that this too was Windows NT.

One underappreciated thing about Windows 8 is that even if the start menu was ugly and blocked the entire screen, you could press the windows key, immediately start typing, and then press enter to somewhat deterministically pick the top app. This made it feel quite fast.

Now on more recent windows editions, I find that I often need to wait for the menu to visually appear before it will accept any keyboard input, and the ranking shifts over time and includes web stuff, making this workflow basically useless.

I also really miss the aero look of windows 7... Eye-candy, sure, but I thought it was pretty, clean and modern looking. I am sad they moved away from it.

That was exactly the same behaviour in Windows 7 though; it wasn't exactly novel. At least Windows 7 searched your apps, and documents all at once. Windows 8 limited you to just apps. Windows 8 was a huge step down in usability.
> One underappreciated thing about Windows 8 is ... you could press the windows key, immediately start typing, and then press enter to somewhat deterministically pick the top app

I agree this is underappreciated but I believe it started in Vista and has worked pretty much the same way ever since, including in Windows 11. I acknowledge that start menu search in general is more bloated now and thus feels less snappy on slower machines. Still, for me, the specific use case you described has worked great for nearly 20 years even on modest PCs. I wonder why my experience doesn't match yours.

> I also really miss the aero look of windows 7... Eye-candy, sure, but I thought it was pretty, clean and modern looking. I am sad they moved away from it.

Me too! Aero was great. I also miss being able to make the taskbar truly black. It looked really nice coupled with a black wallpaper on an OLED display. Now you have to choose from a preset color palette. The reduced customizability of Windows 11 is frustrating.

On fast machines the latency is low enough I don’t complain… but the point about search results shifting is very much a problem. Often times searching a builtin windows feature will fail to show the correct result without some weird switching around of the wording. E.g try searching for “turn windows features on or off”.
When I'm forced to use Windows, I now use Powertoys Run. So I press Alt-Space, then type the name of the app.

It works SO much better than the abomination that the Start Menu has become...

You can even type "%appname" to focus an already running app.

MSFT peaked at Windows 2000.
Was anyone surprised? This follows the classic pattern.

  - XP was good
  - vista was bad
  - 7 was good
  - 8 was bad
  - 10 was good
  - 11 is .....drumroll please.... bad.
I'm pretty sure that Windows 8.1 didn't have a start menu at all, just a windows button that opened that full screen metro launcher