Mac OS X and Windows had their best design language from 2007 to 2011. Windows Aero and Mac OS X Aqua during these days were truly beautiful graphical shells. Everything since has been a barren wasteland of boring, overly white flat GUIs. The squircle-ifying (and on Android, circle-ifying) going on is just another step in this path towards the eternal uniformity of the heat death of fun, intuitive UIs.
The icons for Leopard-era programs were outstanding. Look at that dark indigo ink jar for Pages, or that wormhole graphic for Time Machine. The comforting smooth grey gradient of window title bars, contrasted with the large, globular traffic light buttons. A typeface that worked well with the lower-resolution displays of the time, and unique icons for everything at every single size. Apple actually had a massive human interface guidelines document, which was promptly binned with Yosemite.
On Windows, that dark blue Start orb and the cool dark task bar, signalling a whole new OS experience. The new Welcome Centre. Freshly rewritten programs and new ones like Windows Media Player and Windows Photo Viewer, and the absolute beauty that was the Windows Media Centre. Flip 3D, customising the glass window borders, and the huge, high-resolution 512 × 512 icons of the high-quality, no-ads games shipped with Windows Vista and 7, which still stand up to this day.
For all it's flaws: Vista was a truly breathtakingly beautiful operating system. I still remember fondly the matte frosted dark tinted hue from the start menu and the strong deep red of the shutdown button. Everything shimmered and refracted, with almost a tactile feel. My first iPhone felt like I was interacting beyond the current dimension, the retina display with the skeumorphic design made it feel like I wasn't just interacting with software, I was interacting with another digital world... and my first Macbook was similar; every application was gorgeously rendered natively: something even Windows couldn't manage despite having the lions share of developers.
All this, on LCD panels that were comically abysmal compared to the colour accuracy of the displays we take for granted today, and with less than a quarter of the pixels.
The thing is: I think the same issue plagues software also, that when it becomes a place where good money can be made, you attract people who want to make money and, by necessity, push out all the people who were there for the passion.
Diminishing quality of art and engineering sort of go hand-in-hand if MBAs need to make room for themselves and set up fiefdoms.
I'd say Vista introduced or changed—for the better—a ton of Windows paradigms, most of which still endure. User account control, dwm.exe and the WDDM, improved user profiles, the ribbon UI, and more. Vista had the most pervasive changes to Windows in the past two decades, from UI and UX to fundamental OS primitives, APIs, and syscalls.
Disdain levelled at Vista is unfair—it was a heavyweight OS that needed better hardware than was really commonplace at the time.
As for money now being the end game... I have no words. The stupid Weather app (sorry, no, WebView2 wrapper) on Windows 10 and 11 is exasperating.
The other day we found my wifes laptop from 2009, complete with the original Vista install. Still in hibernation from about 12 years back! Firing up vista is a visual feast. For all its technical and usability offlaws, Microsoft absolutely nailed the aesthetics it.
Another on that hill/cemetary. I remember how mush I wish for a computer that was capable of running Win7 (I was on (P2?) with 512mb of memory and 64mb vram). The OS was a delight from turning it on. I have a friend that has Mavericks on his macbook, and that was another amazing experience.
Even today, you look at screenshots of ios 6, and it's still timelessly beautiful. Some apps were atrocious, but you recognize them from a mile away.
I prefer the less-so but still skeuomorphic designs that pre-dated that period. The default Windows 2000 theme, as well as Mac OS 9, both had just enough drop shadow to make it clear what was and was not clickable, and used just enough color to show what was currently selected or active, without going into the angry fruit cocktail color schemes that pre-dated it in command line programs and followed it up in the super-saturated hyper-skeuomorphic themes of the mid to late aughts.
Luna has better colors, Aero is pale slime colored. Luna has bright green colorful checkbox, Aero has pale slime colored checkbox. Luna has nicely drawn light blue scrollbars, Aero has pale slime colored scrollbars. Luna has colorful warm orange window background, Aero has cold pale slime colored window background. Luna has colorful orange button highlight, Aero has cold slime colored button highlight. Luna has an awesome Power Blade style progress bar, Aero suddenly has a colorful progress bar, but with gimmicky animation of a spinner doing nothing. Luna has colorful gradient window caption, Aero has pale slime colored window caption with gimmicky gloss. Also Aero has too thick window borders.
IIRC Vista had a HIG document to par with Apple's and it's not surprising because they really wanted to change interface and kept it unified. Which worked for the most part but event today, in flat style era there are still 9x widgets deep down below that cannot be rooted out. What they could do was flattening these down.
But with release of Office 2007 and Windows Live suite they started changing interface again and Windows 7 was based upon slight plastic flatness and ribbons all over the place.
There was a community ran project Windows Taskforce that tried to catch up all sorts of interface quirks and with provided mockups they wanted MS to further polish their flagship project between Vista and 7. Sadly all these efforts were gone when MS decided to go Metro in Windows 8.
It's interesting, I always see a lot of love for the more "blobby" (for lack of a better word) UIs from that era, whereas I've always preferred flat UI design. I just think it looks cleaner personally. If the actual functionality of windows wasn't so garbage, I'd really like its more flat UI design in recent times.
Its the same with websites, where I routinely see people unhappy with flat website design, but I deliberately made my website a lot more flat because I think it just looks better. Not to detract from your opinion at all, you can like what you like, but I've just never understood the appeal of vista/xp era UI design over flat design
One thing about the AppleScript icon that you don’t notice until you pay attention is that that the paper curls to form an “S”. The rotation and the reduced emphasis on the paper's edge in the update breaks that imagery.
It's not a nit that has to be picked, but it does dim Apple's "whoa, they thought that through?" aura.
Edit: So, upon doing some more inspection, it looks like Apple's Script Editor already does use this fallen-over paper. So that should challenge our assumptions about what the rotation may or may not mean as a portent for Apple's design competency.
https://help.apple.com/assets/65DFB44F6D920677C90E20C9/65DFB...
The Script Editor logo used to be a physical paper with the AppleScript logo printed on it correctly, but seen at an angle in perspective (so the AppleScript logo was tilted as a result), with a pen on top.
When they switched from the original physical-looking icons, whichever designer drew the new one wasn't paying attention and apparently didn't understand the physical context of the previous logo and they screwed up the revision by keeping the (now-nonsensical) tilt.
Past canaries of Apple's software downfall: Scripting and the new Notification Center.
The key thing to make macOS feel welcoming to everybody from noobs to the nerdiest of power users: Pretty much all functionality used to be accessible using an easy GUI, and keyboard shortcuts, and scripting and command line interface.
At some point Apple Script support started to thin out. I started to worry a bit at this point. Apps that power users care about rely on scripting support. I felt that advanced users have fallen outside the target audience of the product.
Then the new Notification Center came out. And suddenly there was no way of reacting to individual notifications from the keyboard. Two interfaces were no out! No keyboard shortcuts. No scriptability. You HAVE to use the mouse!
Core functionality was suddenly inaccessible using the PRIMARY input device!
How is it possible that the accessibility of such major OS functionality is this poor!
At this point I felt that it's not about target audiences, but about indifference. They don't much care.
Someone once said that monopolies are often never toppled - instead they just become irrelevant over time. This is what happened to Windows. The OS monopoly still exists, but it's no longer the center of anyone's attention.
The same seems to have happened to MacOS. It's as if it has become unimportant inside Apple.
I don't follow him closely, but I'd always thought that John Gruber - while often a very good writer - got a little too much exposure to the Reality Distortion Field. So I'm a little surprised to see him come down so hard on this.
Was I wrong about Gruber or is this a proverbial canary in the coal mine?
Apple enthusiasts like John Gruber believe in an ideal Apple. (See his reference to the Founder's "backs of the cabinets" quote.) The real company is distinct from this ideal. Believers support the company's actions so long as they can be plausibly squared with the ideal. But when the company strays—by phoning in design, or being stingy (iCloud's 5 GB free tier)—they respond with equally vocal criticism.
This comment reminds of me of these such philosophical dualisms:
- Form (Formal Blueprint of Ideas) vs Appearances (Actual Manifestation of Ideas) (Plato)
- Noumenal (how things are in themselves) vs Phenomenal (how things appear) (Immanuel Kant)
Gruber has been an idealistic and longtime Apple observer. This is probably why he seems to invoke the Idea of Apple to compare and critique the current Appearance of Apple.
Fascinated to see a remark on HN that reminds me of this concept in philosophy.
"These are the not the work of carpenters who care about the backs of the cabinets they’re building. These icons are so bad, they look like the work of untrained “How hard can it be?” dilettante carpenters who only last a few days on the job before sawing off one of their own fingers. The whole collection looks like the work from someone with no artistic ability nor an eye for detail. From Apple, of all companies."
Gruber seemed like an Apple sycophant for a while because his values and tastes aligned very closely with Apple's (though he still criticized them from time to time). Now, Apple is drifting away from those values and tastes and so Gruber and others in that sphere of Apple blogs are coming down harder on Apple, especially after Alan Dye made such a mess with "Liquid Glass".
This is the answer. Gruber has and will continue to criticize Apple, but there has generally been very little room for daylight between his values and those of the company (either as expressed in their products or by their leadership). Also, while he doesn't say it, but I suspect that there has long been a feedback loop where his articles defending the company line are well-received internally and have helped him get press access to executives (for his WWDC live show) and preview hardware.
All that said, there has been a marked change since John's "Something Is Rotten in the State of Cupertino". Reading between the lines, it's pretty clear that Apple leadership did not like this article and snubbed him for his liveshow. Since then, there have been many more articles critical of Apple on daringfireball.net.
> especially after Alan Dye made such a mess with "Liquid Glass".
Your comment makes it seem like Gruber is a big critic of Liquid Glass like many commenters on HN are, but that's not the case. He's certainly critical of some of the execution details like icons or translucency that can hinder reading, but his stance on it is pretty nuanced leaning toward cautiously optimistic.
I think it's more the case that Apple is just one of those companies where people tend to leap to the "sycophant" accusation to describe anybody who likes Apple more than a little, because of the (perhaps historical) visibility of their super-fans.
To be frank, Apple earns (earned?) the majority of its applause.
Disk Utility — a very important app — has an icon that’s just an Apple logo (inside the bolt that’s inside the wrench that’s inside the squircle). Not a hard drive, not an external drive, not an SD card. Just an Apple logo.
He is wrong... It's the glass disk that Tim handed over to Donald in the White House.
The NextSTEP people have all retired. The real canary in the coalmine was the release of SwiftUI, which to this day is unusable for real UI work, and yet they keep pushing it. A company that once prided itself on its polished user interfaces, is pushing a fundamentally broken UI framework (they even customized the Swift language itself to make it work!), for no sensible reason, other than to pander to web developers socialized on React.
It's a tired trope, but Steve Jobs is rolling in his grave.
I’m an old school Cocoa dev. I even wrote the UI for a bunch of the built in apps on your iPhone.
I love SwiftUI. I know it inside and out and I’ve talked to its creators. It’s not “done” yet but it is a joy to use. And its power is in saving you from doing “the other 80%” of the work for all the myriad a11y jobs most people don’t bother doing.
Yes of course it panders to web devs. Apple has the same problem MSFT did when webapps with js were invented: if good software can exist in the browser, who cares what OS you have?
SwiftUI is existential for Apple. They are betting the farm on it and Liquid Glass in the hope that native apps are more appealing to users than web apps.
Apple dies if everyone moves to a Google desktop and mobile stack.
Both SwiftUI and Jetpack Compose rewrites, despite all their issues, are still miles ahead on WinUI turned out to be after five years, this is how bad Windows desktop development has become.
UI on Windows is a lost cause at this point. It's over. Windows UI is in the state the Wehrmacht was on April 29, 1945. Fragmented, beaten, disillusioned, out of fuel.
A crescent wrench is a brand of adjustable wrench. I believe Gruber meant open-end wrench, or, because I’m Canadian a British etc roots, I call it a spanner. Either way, I agree the “artist” who drew this has never used such a device, and may not, in fact, qualify as an artist.
> Either way, I agree the “artist” who drew this has never used such a device, and may not, in fact, qualify as an artist.
I was surprised when the article originally leaped to the insane conclusion that someone who created a stylized software icon with (what may not even be) a less-than-perfectly-accurate depiction of a wrench has never used one, but I’m not surprised to see this kind of doubling down on the absurdity from the HN comment section.
Conversely, I disagree; and assert that it is rather John Gruber who has not used nearly enough open ended spanners.
If one has only ever used modern forged steel spanners, then one might think that they aren't this width, and have the jaws at an angle. But try looking at antique tools. There have been a lot of spanners over the past couple of centuries that have looked like the picture.
If I saw a spanner like this in real life, I'd be thinking first half 20th century, possibly from a motorcycling kit, and Imperial and useless. (-:
I don't know if Gruber has ever used a wrench in any serious capacity, because he doesn't mention how the handle in the icons comes exactly at 0 degrees (instead of 15 degrees as in real life.)
As it stands, both the old and the new icons depict handles at 0 degrees, and the old ones depict octagonal open wrenches and not hexagonal ones.
I think it's a mistake to pick apart the wrench icon, but if you're going to make a major issue out of it, at least be exhaustive and consistent in your criticism.
I don’t think anyone is saying it’s a brand of wrench. Just that it is a generic term for a very different kind of wrench with an adjustable jaw. Famous for rounding off the corners of perfectly serviceable nuts, bolts, and all manner of pipe fittings. The wrench in the logo is an open end wrench (typically would have a closed end wrench on the other side)
Does anyone have an example of a design team concluding that the right move is not to change anything?
I really think a big chunk of the problem is that it’s very hard for anyone to say to their employer that they shouldn’t be doing work. People like having a job and finding work not to do feels scary.
Selection bias dictates that if this happens you won’t notice it.
I can think of a few times people have been waiting for a refresh of something only to be slightly disappointed that not much or nothing changed: even when there was really nothing wrong.
Hardware-wise: The Volvo X60 and X90 series of cars.
Software wise: Chrome, perhaps, only one major visual change in 15 years.
The icons for Leopard-era programs were outstanding. Look at that dark indigo ink jar for Pages, or that wormhole graphic for Time Machine. The comforting smooth grey gradient of window title bars, contrasted with the large, globular traffic light buttons. A typeface that worked well with the lower-resolution displays of the time, and unique icons for everything at every single size. Apple actually had a massive human interface guidelines document, which was promptly binned with Yosemite.
On Windows, that dark blue Start orb and the cool dark task bar, signalling a whole new OS experience. The new Welcome Centre. Freshly rewritten programs and new ones like Windows Media Player and Windows Photo Viewer, and the absolute beauty that was the Windows Media Centre. Flip 3D, customising the glass window borders, and the huge, high-resolution 512 × 512 icons of the high-quality, no-ads games shipped with Windows Vista and 7, which still stand up to this day.
Happy to die on this hill defending this opinion.
For all it's flaws: Vista was a truly breathtakingly beautiful operating system. I still remember fondly the matte frosted dark tinted hue from the start menu and the strong deep red of the shutdown button. Everything shimmered and refracted, with almost a tactile feel. My first iPhone felt like I was interacting beyond the current dimension, the retina display with the skeumorphic design made it feel like I wasn't just interacting with software, I was interacting with another digital world... and my first Macbook was similar; every application was gorgeously rendered natively: something even Windows couldn't manage despite having the lions share of developers.
All this, on LCD panels that were comically abysmal compared to the colour accuracy of the displays we take for granted today, and with less than a quarter of the pixels.
The thing is: I think the same issue plagues software also, that when it becomes a place where good money can be made, you attract people who want to make money and, by necessity, push out all the people who were there for the passion.
Diminishing quality of art and engineering sort of go hand-in-hand if MBAs need to make room for themselves and set up fiefdoms.
I'd say Vista introduced or changed—for the better—a ton of Windows paradigms, most of which still endure. User account control, dwm.exe and the WDDM, improved user profiles, the ribbon UI, and more. Vista had the most pervasive changes to Windows in the past two decades, from UI and UX to fundamental OS primitives, APIs, and syscalls.
Disdain levelled at Vista is unfair—it was a heavyweight OS that needed better hardware than was really commonplace at the time.
As for money now being the end game... I have no words. The stupid Weather app (sorry, no, WebView2 wrapper) on Windows 10 and 11 is exasperating.
count me in.
May I throw in BeOs' icons [1] for good measure?
[1]: https://mastodon.social/@allenu/111581402975463677
Even today, you look at screenshots of ios 6, and it's still timelessly beautiful. Some apps were atrocious, but you recognize them from a mile away.
The overdone gloss seemed to be a spiritual copies of all the Windowblinds themes, that were themselves inspired copies of Aqua.
But by God do I miss when icons actually used to represent something visually
But with release of Office 2007 and Windows Live suite they started changing interface again and Windows 7 was based upon slight plastic flatness and ribbons all over the place.
There was a community ran project Windows Taskforce that tried to catch up all sorts of interface quirks and with provided mockups they wanted MS to further polish their flagship project between Vista and 7. Sadly all these efforts were gone when MS decided to go Metro in Windows 8.
Do you have screenshots of the particular versions you're talking about?
As for Time Machine, a screenshot won't do it justice[2].
[1]: https://mastodon.social/@BasicAppleGuy/115033200191662888
[2]: https://youtu.be/1BOwL8MuE_Y
Its the same with websites, where I routinely see people unhappy with flat website design, but I deliberately made my website a lot more flat because I think it just looks better. Not to detract from your opinion at all, you can like what you like, but I've just never understood the appeal of vista/xp era UI design over flat design
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Dead Comment
It's not a nit that has to be picked, but it does dim Apple's "whoa, they thought that through?" aura.
Edit: So, upon doing some more inspection, it looks like Apple's Script Editor already does use this fallen-over paper. So that should challenge our assumptions about what the rotation may or may not mean as a portent for Apple's design competency. https://help.apple.com/assets/65DFB44F6D920677C90E20C9/65DFB...
When they switched from the original physical-looking icons, whichever designer drew the new one wasn't paying attention and apparently didn't understand the physical context of the previous logo and they screwed up the revision by keeping the (now-nonsensical) tilt.
https://web.archive.org/web/20101207035423if_/http://upload....
And we would have laughed at it.
The key thing to make macOS feel welcoming to everybody from noobs to the nerdiest of power users: Pretty much all functionality used to be accessible using an easy GUI, and keyboard shortcuts, and scripting and command line interface.
At some point Apple Script support started to thin out. I started to worry a bit at this point. Apps that power users care about rely on scripting support. I felt that advanced users have fallen outside the target audience of the product.
Then the new Notification Center came out. And suddenly there was no way of reacting to individual notifications from the keyboard. Two interfaces were no out! No keyboard shortcuts. No scriptability. You HAVE to use the mouse!
Core functionality was suddenly inaccessible using the PRIMARY input device!
How is it possible that the accessibility of such major OS functionality is this poor!
At this point I felt that it's not about target audiences, but about indifference. They don't much care.
Someone once said that monopolies are often never toppled - instead they just become irrelevant over time. This is what happened to Windows. The OS monopoly still exists, but it's no longer the center of anyone's attention.
The same seems to have happened to MacOS. It's as if it has become unimportant inside Apple.
Was I wrong about Gruber or is this a proverbial canary in the coal mine?
- Form (Formal Blueprint of Ideas) vs Appearances (Actual Manifestation of Ideas) (Plato)
- Noumenal (how things are in themselves) vs Phenomenal (how things appear) (Immanuel Kant)
Gruber has been an idealistic and longtime Apple observer. This is probably why he seems to invoke the Idea of Apple to compare and critique the current Appearance of Apple.
Fascinated to see a remark on HN that reminds me of this concept in philosophy.
"These are the not the work of carpenters who care about the backs of the cabinets they’re building. These icons are so bad, they look like the work of untrained “How hard can it be?” dilettante carpenters who only last a few days on the job before sawing off one of their own fingers. The whole collection looks like the work from someone with no artistic ability nor an eye for detail. From Apple, of all companies."
https://www.macrumors.com/2025/05/29/no-apple-executives-tal...
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Dead Comment
All that said, there has been a marked change since John's "Something Is Rotten in the State of Cupertino". Reading between the lines, it's pretty clear that Apple leadership did not like this article and snubbed him for his liveshow. Since then, there have been many more articles critical of Apple on daringfireball.net.
Your comment makes it seem like Gruber is a big critic of Liquid Glass like many commenters on HN are, but that's not the case. He's certainly critical of some of the execution details like icons or translucency that can hinder reading, but his stance on it is pretty nuanced leaning toward cautiously optimistic.
https://daringfireball.net/linked/2025/06/09/apple-intro-liq...
For that reason, even if one thought he agreed with Apple too often at least one always knew why.
I'll add that the blue one doesn't even look like a wrench. I know that the old icons are dated and need to go, but the new ones are just bad.
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To be frank, Apple earns (earned?) the majority of its applause.
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Gruber has criticized Apple, but never to this extent.
He is wrong... It's the glass disk that Tim handed over to Donald in the White House.
It's a tired trope, but Steve Jobs is rolling in his grave.
I love SwiftUI. I know it inside and out and I’ve talked to its creators. It’s not “done” yet but it is a joy to use. And its power is in saving you from doing “the other 80%” of the work for all the myriad a11y jobs most people don’t bother doing.
Yes of course it panders to web devs. Apple has the same problem MSFT did when webapps with js were invented: if good software can exist in the browser, who cares what OS you have?
SwiftUI is existential for Apple. They are betting the farm on it and Liquid Glass in the hope that native apps are more appealing to users than web apps.
Apple dies if everyone moves to a Google desktop and mobile stack.
I was surprised when the article originally leaped to the insane conclusion that someone who created a stylized software icon with (what may not even be) a less-than-perfectly-accurate depiction of a wrench has never used one, but I’m not surprised to see this kind of doubling down on the absurdity from the HN comment section.
If one has only ever used modern forged steel spanners, then one might think that they aren't this width, and have the jaws at an angle. But try looking at antique tools. There have been a lot of spanners over the past couple of centuries that have looked like the picture.
If I saw a spanner like this in real life, I'd be thinking first half 20th century, possibly from a motorcycling kit, and Imperial and useless. (-:
As it stands, both the old and the new icons depict handles at 0 degrees, and the old ones depict octagonal open wrenches and not hexagonal ones.
I think it's a mistake to pick apart the wrench icon, but if you're going to make a major issue out of it, at least be exhaustive and consistent in your criticism.
"Hey, it's just an icon, not working wrench after all"
That there is a open-end wrench, or half a combination wrench.
(It could be a crow's foot but we'll leave that aside.)
I really think a big chunk of the problem is that it’s very hard for anyone to say to their employer that they shouldn’t be doing work. People like having a job and finding work not to do feels scary.
I can think of a few times people have been waiting for a refresh of something only to be slightly disappointed that not much or nothing changed: even when there was really nothing wrong.
Hardware-wise: The Volvo X60 and X90 series of cars.
Software wise: Chrome, perhaps, only one major visual change in 15 years.