Steve Jobs is famous for his 1996 quote about Microsoft not having taste (https://www.youtube.com/watch?v=UiOzGI4MqSU). I disagree; as much as I love the classic Mac OS and Jobs-era Mac OS X, and despite my feelings about Microsoft's monopolistic behavior, 1995-2000 Microsoft's user interfaces were quite tasteful, in my opinion, and this was Microsoft's most tasteful period. I have fond memories of Windows 95/NT 4/98/2000, Office 97, and Visual Basic 6. I even liked Internet Explorer 5. These were well-made products when it came to the user interface. Yes, Windows 95 crashed a lot, but so did Macintosh System 7.
Things started going downhill, in my opinion, with the Windows XP "Fisher-Price" Luna interface and the Microsoft Office 2007 ribbon.
Ribbon also has a similar research behind it, just like Windows 95. For what they designed it, allowing beginners to discover all the functionality that's available, it works perfectly.
I think most of the complaints from the tech circles are completely unfounded in reality. Many non-tech people and younger ones actually prefer using Ribbon. I also like it since it is very tastefully made for Office. 2010 was my favorite Office UI. It actually doesn't get rid of shortcuts either. Most of the Office 2003 ones were preserved to not break the workflow of power users.
Where Ribbon doesn't work is when you take out the contextual activation out of it. Most companies copied it in a very stupid way. They just copied how it looks. The way it is implemented in Sibelius, WinDBG or PDFXChange is very bad.
By your timeline, it means Microsoft only had institutional taste for about 3-4 years. A tiny fraction of the company’s lifetime.
(If it helps, I do agree with you about those years being the most… design-coordinated: when Office felt like part of Windows)
(I like to think that Visual Studio 2026 proves that the company can still do good desktop UI design; but it doesn’t help that every major first-party product is now using their own silo’d UI framework; wither MFC and CommonControls, I guess)
Windows 95 was a vast improvement in looks over 3.x. Of course tastes differ, but I found it very aesthetic, not ugly at all, and used the classic look until Windows 7 EOLd.
> 1995-2000 Microsoft's user interfaces were quite tasteful
Only because they copied NeXTSTEP. Those 3D beveled controls originated in NeXTSTSP. In Windows, ctl3d.dll added raised and sunken 3D-looking buttons, beveled text boxes, group boxes with depth, a light-source illusion using highlight and shadow, all copied from NeXTSTEP.
please recall that 8bit color was the common capability for CRT displays at that time. Simple one bit display was also common. Any smooth transitions in gray or color had to use dithering, or be very clever in the way they chose the palate.
Certainly some historic credit goes to Motif, but, there are "levels to this game" .. Motif did not jump out as "wow that looks good" IMHO. Obviously NeXT was extreme in a different way.. sort of like a symphony orchestra more than an office machine.
It is genuinely entertaining to see people defend the dull and pedestrian UI in Windows 95.
I'm a huge fan of the book "Design for the Real World" by Victor Papanek. One of the things that he talked about is the importance of using materials honestly: not trying to pass plastic off as wood, using the given material to it's best ability (even if itis plastic).
I've always thought the Windows 3.1 to Win2K era were exactly that. The medium is pixels on a screen, the mouse and keyboard. And there is no artifice, it's just the bare essentials.
Look how crisp, professional, and usable it all is.
This is a very good write-up. There's no way this level of testing and dedication could have resulted in the execrable shitshow that is Windows today.
Mac OS is going backward with accelerating speed, too. They had just started to recover from Jony Ive when they put a packaging designer in charge of UI... resulting in the "Liquid Glass" debacle, and all the other incompetent UI changes that accompanied Tahoe's rollout.
To be fair, Apple has always had a penchant for removing important features because they don't like how they look. I cannot count how many times I got a CD/DVD stuck in a Mac, and due to a lack of physical eject button and the software eject button not working, resorted to the emergency eject sequences. Just put a button to eject the disk, ffs.
Designers tend to be less open to feedback than developers. That, I think, helps explain why flat UI persists even though it has shown usability drawbacks. It also helps explain why overall usability feels like it's declining ever year — for instance, macOS Tahoe seems noticeably worse in usability compared to macOS Sequoia. Does anyone think Apple is going to rush out a release that fixes the excessive rounding of window corners? Don't hold your breath.
Once the windows become actually circles, or maybe some point along that path, they'll go back to square corners and congratulate themselves on how much better and innovative they are. It's just a stupid trend to keep rounding things more and more... I hope.
On the topic of flat design specifically, developers are likely just as culpable. Back when it was just starting to catch on, by my observation some of the quickest to adopt it were solo developers because it's way easier to build a passable looking app with flat UI since that doesn't require any design talent.
I don't think openness to feedback is the main metric, but rather ability to objectively measure outcomes. It's just harder to objectively measure usability than the presence or absence of a bug or performance problem.
It's all just rearranging deck chairs at this point.
I feel like UX designers don't realize that their job should have a natural tailing off as we discover and lock in the good ideas and discard the bad. Even if the ideas aren't that great, users can at least get good at however it does work, if it stays constant. Instead, we just get more dice rolls, eyecandy, and frustration.
I for one hate the power dynamic that OS and website designers have over me. They can just sneak into my house and rearrange my furniture on a whim. Even if it sucks, I would adapt to it if it stayed constant! Instead I both hate it and can't learn it, because everything is different and keeps changing when I least expect it.
At this point my brain has given into learned helplessness and won't retain much of anything at all, but it's next-level figured out that it's useless.
Designers seem to have a bad track record, and it's getting worse.
> The Windows 95 user interface design team was formed in October, 1992... The number of people oscillated during the project but was approximately twelve. The software developers dedicated to implementing the user interface accounted for another twelve or so people
I still don't understand what happened starting around 2010-ish (from my observations at the time) that we went from being able to handle a company's worth of software with 30 people, to needing 30 people for every individual project. Startups with minor products had team-pages with 15 people.
I think Windows 95/2000 and the contemporary MacOS (including the then future MacOS X) have the best UI in everything I used in my 30+ years of tech life.
I sincerely hope that one day we could go back to that road. If you want that achieved, please support me to join Apple/Microsoft to become the UI boss, fire all flat-design people and hire a small team to implement the older UI, then give a few passionate talks on EDX and conferences so people who supported flat UI magically support the older UI. They always follow whoever the lead is like headless flies.
After nearly 30 years of tech life myself, I've come to the realization that the best UIs are not graphical. They can have graphical elements mostly for visualization purposes, but all of them should be as minimal and unobtrusive as possible. Any interactivity should be primarily keyboard-driven, and mouse input should be optional.
Forcing users to click on graphical elements presents many challenges: what constitutes an "element"; what are its boundaries; when is it active, inactive, disabled, etc.; if it has icons, what do they mean; are interactive elements visually distinguishable from non-interactive elements; and so on.
A good example of bad UI that drives me mad today on Windows 11 is something as simple as resizing windows. Since the modern trend is to have rounded corners on everything, it's not clear where the "grab" area for resizing a window exists anymore. It seems to exist outside of the physical boundary of the window, and the actual activation point is barely a few pixels wide. Apparently this is an issue on macOS as well[1].
Like you, I do have a soft spot for the Windows 2000 GUI in particular, and consider it the pinnacle of Microsoft's designs, but it still feels outdated and inneficient by modern standards. The reason for this is because it follows the visual trends of the era, and it can't accomodate some of the UX improvements newer GUIs have (universal search, tiled/snappable windows, workspaces, etc.).
So, my point is that eschewing graphics as much as possible, and relying on keyboard input to perform operations, gets rid of the graphical ambiguities, minimizes the amount of trend following making the UI feel timeless, and makes the user feel more in command of their experience, making them more efficient and quicker.
This UI doesn't have to be some inaccessible CLI or TUI, although that's certainly an option for power users, but it should generally only serve to enable the user to do their work as easily as possible, and get out of the way the rest of the time. Unfortunately, most modern OSs have teams of designers and developers that need to justify their salary, and a UI that is invisible and rarely changes won't get anyone promoted. But it's certainly possible for power users to build out this UI themselves using some common and popular software. It takes a bit of work, but the benefits far outweigh the time and effort investment.
Yep. I always cite XP as being Windows's peak, but I forgot that it shipped with their insulting Fisher-Price motif enabled by default. Step 1 was to switch the UI to "classic" (essentially Windows 95) mode, and all was well.
Windows 95 is a great case study because with that release, Microsoft did more for GUIs than Apple did through the entire decade of the '90s... and beyond.
All of it is now out the window (pun invited). It's a race to the bottom between Microsoft and Apple, with Microsoft having a HUGE head-start. But Apple has really stepped up to the plate with Tahoe, crippling it with big enough UI blunders to keep them in the enshittification game.
I really liked XP (and 7) because for me, having a capable theming engine built in that didn't take a ton of extra resources or cause instability (unlike Stardock's WindowBlinds) was a real value add. There were some absolutely gorgeous third party XP/Vista/7 themes on sites like DeviantArt that worked extremely well within the limits of the engine, had a unique look and feel, and were just as usable as the "classic" theme.
When MS gutted the theming engine with the release of Windows 8 (flat rectangles only) I was devastated.
The engine itself isn’t gutted - it’s full of functionality that was never lost. MS just (correctly) reasoned that transparency effects in the UI - introduced in Vista simply to show-off the capabilities of the DWM compositor - ultimately detract from a good UI.
Usability is the wrong metric, paint by numbers is more "usable" (sic accessible) than a canvas but you'd be depressed watching your son graduate art school and that's all he can do.
If you do want to optimize for usability you have to make sure you aren't making the system more consumptive at the same time. The prime example from the article is trading a moment where the user must take initiative with a menu. More useable less useful. Lower the floor not the ceiling etc. Windows (and iOS) did make genuine improvements to OSs but because of decisions like these most users are locked out of enjoying them.
Steve Jobs is famous for his 1996 quote about Microsoft not having taste (https://www.youtube.com/watch?v=UiOzGI4MqSU). I disagree; as much as I love the classic Mac OS and Jobs-era Mac OS X, and despite my feelings about Microsoft's monopolistic behavior, 1995-2000 Microsoft's user interfaces were quite tasteful, in my opinion, and this was Microsoft's most tasteful period. I have fond memories of Windows 95/NT 4/98/2000, Office 97, and Visual Basic 6. I even liked Internet Explorer 5. These were well-made products when it came to the user interface. Yes, Windows 95 crashed a lot, but so did Macintosh System 7.
Things started going downhill, in my opinion, with the Windows XP "Fisher-Price" Luna interface and the Microsoft Office 2007 ribbon.
> Microsoft Office 2007 ribbon
Ribbon also has a similar research behind it, just like Windows 95. For what they designed it, allowing beginners to discover all the functionality that's available, it works perfectly.
I think most of the complaints from the tech circles are completely unfounded in reality. Many non-tech people and younger ones actually prefer using Ribbon. I also like it since it is very tastefully made for Office. 2010 was my favorite Office UI. It actually doesn't get rid of shortcuts either. Most of the Office 2003 ones were preserved to not break the workflow of power users.
Where Ribbon doesn't work is when you take out the contextual activation out of it. Most companies copied it in a very stupid way. They just copied how it looks. The way it is implemented in Sibelius, WinDBG or PDFXChange is very bad.
By your timeline, it means Microsoft only had institutional taste for about 3-4 years. A tiny fraction of the company’s lifetime.
(If it helps, I do agree with you about those years being the most… design-coordinated: when Office felt like part of Windows)
(I like to think that Visual Studio 2026 proves that the company can still do good desktop UI design; but it doesn’t help that every major first-party product is now using their own silo’d UI framework; wither MFC and CommonControls, I guess)
I think there is distinction there between look and functionality.
They were functionally just fine; good even compared to some modern abominations.
But the look was just plain and ugly, even compared to some alternatives at the time.
> Things started going downhill, in my opinion, with the Windows XP "Fisher-Price" Luna interface and the Microsoft Office 2007 ribbon.
Yeah I just ran it with 2000-compatible look; still ugly but at least not wasting screen space
Windows 95 was a vast improvement in looks over 3.x. Of course tastes differ, but I found it very aesthetic, not ugly at all, and used the classic look until Windows 7 EOLd.
> 1995-2000 Microsoft's user interfaces were quite tasteful
Only because they copied NeXTSTEP. Those 3D beveled controls originated in NeXTSTSP. In Windows, ctl3d.dll added raised and sunken 3D-looking buttons, beveled text boxes, group boxes with depth, a light-source illusion using highlight and shadow, all copied from NeXTSTEP.
That’s an odd way to spell Motif.
Motif 1.0 shipped in 1990. NeXTSTEP in 1988 had 3D beveled controls. So I believe I got the spelling right :)
please recall that 8bit color was the common capability for CRT displays at that time. Simple one bit display was also common. Any smooth transitions in gray or color had to use dithering, or be very clever in the way they chose the palate.
Certainly some historic credit goes to Motif, but, there are "levels to this game" .. Motif did not jump out as "wow that looks good" IMHO. Obviously NeXT was extreme in a different way.. sort of like a symphony orchestra more than an office machine.
It is genuinely entertaining to see people defend the dull and pedestrian UI in Windows 95.
I'm a huge fan of the book "Design for the Real World" by Victor Papanek. One of the things that he talked about is the importance of using materials honestly: not trying to pass plastic off as wood, using the given material to it's best ability (even if itis plastic).
I've always thought the Windows 3.1 to Win2K era were exactly that. The medium is pixels on a screen, the mouse and keyboard. And there is no artifice, it's just the bare essentials.
Look how crisp, professional, and usable it all is.
This is a very good write-up. There's no way this level of testing and dedication could have resulted in the execrable shitshow that is Windows today.
Mac OS is going backward with accelerating speed, too. They had just started to recover from Jony Ive when they put a packaging designer in charge of UI... resulting in the "Liquid Glass" debacle, and all the other incompetent UI changes that accompanied Tahoe's rollout.
To be fair, Apple has always had a penchant for removing important features because they don't like how they look. I cannot count how many times I got a CD/DVD stuck in a Mac, and due to a lack of physical eject button and the software eject button not working, resorted to the emergency eject sequences. Just put a button to eject the disk, ffs.
I hate liquid glass with a burning passion. I've never understood why people get so irritated at design changes until now.
Sadly, it won't be the last time you'll feel that angry passion.
I like to jest that packaging designer would of course wrap things in clear plastic...
Designers tend to be less open to feedback than developers. That, I think, helps explain why flat UI persists even though it has shown usability drawbacks. It also helps explain why overall usability feels like it's declining ever year — for instance, macOS Tahoe seems noticeably worse in usability compared to macOS Sequoia. Does anyone think Apple is going to rush out a release that fixes the excessive rounding of window corners? Don't hold your breath.
Once the windows become actually circles, or maybe some point along that path, they'll go back to square corners and congratulate themselves on how much better and innovative they are. It's just a stupid trend to keep rounding things more and more... I hope.
On the topic of flat design specifically, developers are likely just as culpable. Back when it was just starting to catch on, by my observation some of the quickest to adopt it were solo developers because it's way easier to build a passable looking app with flat UI since that doesn't require any design talent.
I don't think openness to feedback is the main metric, but rather ability to objectively measure outcomes. It's just harder to objectively measure usability than the presence or absence of a bug or performance problem.
It's all just rearranging deck chairs at this point.
I feel like UX designers don't realize that their job should have a natural tailing off as we discover and lock in the good ideas and discard the bad. Even if the ideas aren't that great, users can at least get good at however it does work, if it stays constant. Instead, we just get more dice rolls, eyecandy, and frustration.
I for one hate the power dynamic that OS and website designers have over me. They can just sneak into my house and rearrange my furniture on a whim. Even if it sucks, I would adapt to it if it stayed constant! Instead I both hate it and can't learn it, because everything is different and keeps changing when I least expect it.
At this point my brain has given into learned helplessness and won't retain much of anything at all, but it's next-level figured out that it's useless.
Designers seem to have a bad track record, and it's getting worse.
Sorry, designers.
Past discussion:
https://news.ycombinator.com/item?id=12330899
Thanks! Macroexpanded...
The Windows 95 User Interface: A Case Study in Usability Engineering (1996) - https://news.ycombinator.com/item?id=12330899 - Aug 2016 (72 comments)
This part stands out to me:
> The Windows 95 user interface design team was formed in October, 1992... The number of people oscillated during the project but was approximately twelve. The software developers dedicated to implementing the user interface accounted for another twelve or so people
I still don't understand what happened starting around 2010-ish (from my observations at the time) that we went from being able to handle a company's worth of software with 30 people, to needing 30 people for every individual project. Startups with minor products had team-pages with 15 people.
Microsoft had thousands of people working on Windows. Sun Microsystems had thousands of people working on Java.
Yes and with all these huge and siloed teams you end up with no consistency even within a single app
Everything since this style of design feels like a cartoon version, with ridiculous non-sense that only gets in the way.
I think Windows 95/2000 and the contemporary MacOS (including the then future MacOS X) have the best UI in everything I used in my 30+ years of tech life.
I sincerely hope that one day we could go back to that road. If you want that achieved, please support me to join Apple/Microsoft to become the UI boss, fire all flat-design people and hire a small team to implement the older UI, then give a few passionate talks on EDX and conferences so people who supported flat UI magically support the older UI. They always follow whoever the lead is like headless flies.
LOL.
After nearly 30 years of tech life myself, I've come to the realization that the best UIs are not graphical. They can have graphical elements mostly for visualization purposes, but all of them should be as minimal and unobtrusive as possible. Any interactivity should be primarily keyboard-driven, and mouse input should be optional.
Forcing users to click on graphical elements presents many challenges: what constitutes an "element"; what are its boundaries; when is it active, inactive, disabled, etc.; if it has icons, what do they mean; are interactive elements visually distinguishable from non-interactive elements; and so on.
A good example of bad UI that drives me mad today on Windows 11 is something as simple as resizing windows. Since the modern trend is to have rounded corners on everything, it's not clear where the "grab" area for resizing a window exists anymore. It seems to exist outside of the physical boundary of the window, and the actual activation point is barely a few pixels wide. Apparently this is an issue on macOS as well[1].
Like you, I do have a soft spot for the Windows 2000 GUI in particular, and consider it the pinnacle of Microsoft's designs, but it still feels outdated and inneficient by modern standards. The reason for this is because it follows the visual trends of the era, and it can't accomodate some of the UX improvements newer GUIs have (universal search, tiled/snappable windows, workspaces, etc.).
So, my point is that eschewing graphics as much as possible, and relying on keyboard input to perform operations, gets rid of the graphical ambiguities, minimizes the amount of trend following making the UI feel timeless, and makes the user feel more in command of their experience, making them more efficient and quicker.
This UI doesn't have to be some inaccessible CLI or TUI, although that's certainly an option for power users, but it should generally only serve to enable the user to do their work as easily as possible, and get out of the way the rest of the time. Unfortunately, most modern OSs have teams of designers and developers that need to justify their salary, and a UI that is invisible and rarely changes won't get anyone promoted. But it's certainly possible for power users to build out this UI themselves using some common and popular software. It takes a bit of work, but the benefits far outweigh the time and effort investment.
[1]: https://news.ycombinator.com/item?id=46579864
Yep. I always cite XP as being Windows's peak, but I forgot that it shipped with their insulting Fisher-Price motif enabled by default. Step 1 was to switch the UI to "classic" (essentially Windows 95) mode, and all was well.
Windows 95 is a great case study because with that release, Microsoft did more for GUIs than Apple did through the entire decade of the '90s... and beyond.
All of it is now out the window (pun invited). It's a race to the bottom between Microsoft and Apple, with Microsoft having a HUGE head-start. But Apple has really stepped up to the plate with Tahoe, crippling it with big enough UI blunders to keep them in the enshittification game.
I really liked XP (and 7) because for me, having a capable theming engine built in that didn't take a ton of extra resources or cause instability (unlike Stardock's WindowBlinds) was a real value add. There were some absolutely gorgeous third party XP/Vista/7 themes on sites like DeviantArt that worked extremely well within the limits of the engine, had a unique look and feel, and were just as usable as the "classic" theme.
When MS gutted the theming engine with the release of Windows 8 (flat rectangles only) I was devastated.
The engine itself isn’t gutted - it’s full of functionality that was never lost. MS just (correctly) reasoned that transparency effects in the UI - introduced in Vista simply to show-off the capabilities of the DWM compositor - ultimately detract from a good UI.
Notice how they moved the ok & cancel buttons to the bottom right since it’s the more logical location to put them.
Meanwhile gtk now puts those on opposite sides of the window title bar by default.
Usability is the wrong metric, paint by numbers is more "usable" (sic accessible) than a canvas but you'd be depressed watching your son graduate art school and that's all he can do.
If you do want to optimize for usability you have to make sure you aren't making the system more consumptive at the same time. The prime example from the article is trading a moment where the user must take initiative with a menu. More useable less useful. Lower the floor not the ceiling etc. Windows (and iOS) did make genuine improvements to OSs but because of decisions like these most users are locked out of enjoying them.