I'll also give the opinion that Apple consistently creates some absolutely crap designs and when they do this, release something really really mind mindbogglingly stupid that it should be embarrassing they are instead met with applause on the "amazing design". It's a tiresome pattern repeated for decades now.

eg. The 'breathing status light' that lit up the room at night due to extreme brightness which meant every macbook of the era had stickers or tape over the LED with endless Q&A's of "How do i turn the annoying light off? You can't!". This crap design was met by articles extolling the subtle sign wave and off white hue. I kid you not. https://avital.ca/notes/a-closer-look-at-apples-breathing-li...

Apple today seem to have acknowledged their mistake here and taken away status lights completely (also a crappy design hailed as amazing since they've just gone to the other extreme) which highlights the fact that no matter what they do they're hailed as being amazing at design, even when it's contradictory from their own previous 'amazing designs'.

Apple doesn't just get a pass on crappy design. It gets endless articles praising the virtues of everything they do even when, if you think about what they did for even a second you'd realize, "that's actually just plain crap design".

> 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.

People need to go back and use Win 3.1 or MacOS 7.x to realize what a leap forward Win95 was. MacOS 7.x didn't even have preemptive multitasking! The start menu and task bar made their debut and immediately anchored the whole UI. Since then, Windows has made incremental advances (with the occasional step backwards), but no change has been nearly so radical. OS X would not have been possible without the influence of win95. We're still living in the Win95 age.

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

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)

MS may not have been as tasteful as MacOS, but the functionality was at least there and it was easy to find and use. That goes a long way to make up for the bland-ish look.

Then we lost even more taste, and eventually the functionality and user friendlyness, on both sides of the isle.

> 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.

What made system 7 and 8 worse in some respect was when it crashed, it crashed hard without warning

With windows the crash was progressive so you have time to save and prepare.

I also have fond memories of windows 2000. It was rock steady and polished. I preferred it over system 8 and even OS X which had to many Unix conventions.

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.

Ranting on UI, I think I might blame MS for this but I feel like many shortcuts for customization in apps and OS are a net negative.

The first example I remember was ~2003ish when MS Office did a big redesign and got much bigger toolbars. That they were big is a matter of taste but that's not where I'm going with this. No, the issue was that they made too easy to ACCIDENTALLY mess up the UI. They added all kinds of customization (which is fine) but then made it so just dragging a little too long an a button would let you move the button somewhere else. So, grandpa drags the button, possible off the bar, deleting it, and now for all intents and purposes the app is unusable to him. IMO, the customization options should be buried deeper where they can't happen by accident.

This "ACCIDENTAL" modification is all the rage now. On iPhone, holding on the lock screen puts the phone in "edit the lock screen mode". Several family members have asked why the image they put on the lock screen was gone. It was because they "butt edited the screen". Put the phone in their pocket and it felt a press and went into edit mode and edited the lock screen. AFAIK, almost no one needs this shortcut. It would be fine to just go into Settings->Wallpaper->Lockscreen or something like that. But, I'm just guessing (1) some UX designer needed something todo (2) someone working on lockscreen options got tired of doing the Settings->Wallpaper->Lockscreen dance and put in a shortcut that no-one but them needs.

This same issue is all over the place. The iPhone's lockscreen while charging mode has the same issue. The user (me) picks the clock face I want. And, one of 10 times I reach for the phone from the charging stand I accidently touch the screen which changes the face. I NEVER NEED THIS. Again, this should be buried in Settings->Lockscreen->Clock Face. The shortcut a net negative.

There are many more.

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.

I like to jest that packaging designer would of course wrap things in clear plastic...

Looking forward to your talk.

I feel like there's a taste issue which is similar to tabs vs spaces or other coding styles. Some languages kind of solve this with auto-formatting but just because they choose a standard doesn't mean their standard is as readable as some other.

In languages one taste issue that comes to mind. Many languages have the invisible scope issue

    foo = bar

Me though, I want the line to be understandable with as little external context as possible. I don't want to have to dig up 10, 50, 100 lines to see if a local foo has been defined or if it's member. So like python or typescript. I like foo has to be this.foo or self.foo if you want it assign the current object's member. Most programmers seem to agree because they end up using mFoo or foo_ or some naming convention to work around the issue but I think I'd prefer the language to enforce it.

I don't know which if any languages make all the different scopes more explicit.

So far I haven't liked Swift though which seems more explicit. Even though it's more explicit in some areas I feel like the majority of my time is typing boilerplate and fixing trivial syntax errors. I know programming requires syntax and, as an example, I include semicolons everywhere in JavaScript even though they are not required. That said, I would like to get all the time back in my life where I compiled some C++ only to be told "error: missing semicolon at end of class definition" or "error: extra semicolon at end of member function declaration". It feels like a language should fix this stuff for the dumb human rather than make the human do random tedious work. I get there might be times where it's ambiguous but I wonder if it's also a language design issue.

Ok, except operating a commercial airliner literally takes thousands of hours of training, requires an extremely detailed mental model for how air flight works, and heavily relies on external procedures like checklists to ensure safe operation.

And fatal accidents due to poorly thought out control systems do occur.

https://www.fastcompany.com/1669720/how-lousy-cockpit-design...

Also fwiw using the word "intuitive" is an instant sign of someone not being a great designer.

https://www.asktog.com/papers/raskinintuit.html

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 think you might be confusing flat design with UI density. While they emerged as trends during a similar period, they are distinct concepts. You can have small flat elements or large skeuomorphic ones.

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.

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.

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)

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.

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

Separating them is good for avoiding misclicks.

Decades ago, MacOS properly had the close box for windows on the opposite side from minimize etc. widgets; now the one destructive window action could be reasonably safe without confirmation. Then Windows started gaining popularity and nobody ever did it the right way by default again. A pity for the sharp minds at Xerox PARC.

Both OS lines were developed concurrently up until XP release where DOS-based 9x was abandoned and NT became the basis for every subsequent product. Plus of course there's that whole part of the story where MS teamed up with IBM and worked on OS/2.

NT got new 9x shell with 4.0 release but a beta package could be installed on 3.51 as well - tho, that could render some compatibility issues.

No, Windows NT until 4.0 had the same interface design as Windows 3.x (although there existed a semi-official SP/addon to give NT 3.5 the Chicago interface, making it quite similar to 95), and NT 4.0 came later than 95

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