It looks like someone getting good at illustration. Older icons are far better illustrations. However icon design is not just about illustration, it's about clarity and affordances. Icons don't exist in isolation like an illustration, they exist alongside the rest of the UX and other app icons, and being recognisable is important.
All that to say, the sweet pot was likely somewhere in the middle of this timeline. The earliest icons aren't recognisable enough as they're too illustrative. The later icons aren't recognisable enough because they're too basic. The middle are pretty, clear from colour, clear from shape, well branded.
Designer here: there's a trade-off between visual harmony (all icons look the same) and ease of differentiation.
A standardized container adds regularity to irregular shapes.
Recently, Apple has been heavily opting for visual harmony, so their icons look consistent when seen as a set. Google too. It's an industry trend that is fairly annoying.
Similar "let's remove the differentiation" decision made for menu icons in macOS: https://tonsky.me/blog/tahoe-icons/
I prefer illustrations and old school icons. Every icon was unique and easily recognizable.
Now all icons look alike, and it takes longer to recognize.
I agree with your conclusion that the sweet spot is in the middle, because I could easily explain to my mom "click the icon that has a pen and paper" and it would be very obvious. The current icon is completely ambiguous crap.
The fact that since Tahoe everything is a squircle kills me. I can’t visually find my apps anymore.
It takes me several seconds to find an existing opened app when I hit cmd tab, it has been months already, I use my Mac for work, I know this stuff.
It’s not just the new design but also something else, like if part of my Mac lost its soul.
The new one, orange pen on black background, to me looks like a blacksmith hammer or a welding torch.
I would not associate it with writing at all.
2, 3, and 4 (from the left) look like they're for a notes app rather than DTP.
5 and 6 tell me what the app is for.
7 looks like an art app, not writing. I favour skeumorphism, but to work that needs to use metaphors people are familiar with, and pots of ink are something I know only from art stores.
None of the Pages icons are recognisable because almost no one uses Pages. The word icon is just a blue W which is not any more illustrative than an orange pen.
I actually had to try to zoom in on the older, “ideal” example shown, just to see what it is.
Yes, my eyes aren’t great anymore. Yes, I’m on my phone looking at a social media post. But I feel like the speed and clarity of the newer ones was (accidentally) on display here.
Anyone else doesn't like modern minimalist icon design? It looks boring.
Latest icons are also horrible. Magnifying glass for "open containing directory".
I agree. The middle one seems to be the best combination of clarity and simplicity.
Tbh I like the far left way more than the rest. It is simple, clear, and distinctive.
Dead middle is decent too.
How in the world are the newer icons more clear?
They are hard to distinguish from each other, removing the main goal of an icon…to make it easy and quick to uniquely identify an app.
Exactly.
Anyone who thinks an intricate illustration of a quill and ink communicates to the user "Hey this app is our Microsoft Word"...is not thinking about what function an icon is supposed to serve.
It's like comparing a road sign to an 18th century painting and saying "LOOK HOW FAR WE'VE FALLEN!"
These are not serious people.
I spent half a year designing and creating 200+ icons for a custom geospatial mapping app. I really enjoyed the work but it was grueling and tedious, especially the design part. Too many people had too many different opinions on which symbols meant what, which styles clearly conveyed ideas without being too detailed, and many other things that kept wasting my time and causing a lot of rework and inconsistencies. It was literally just me doing the work, so I stopped trying to get consensus and took a few weeks to redesign the entire set and even used color science to inform my design decisions. I created the entire set without external input, then presented it. Sure there was some tweaking here and there, but I believe it turned about to be great and no one really complained in the end. The most important part was that end-users were happy. I used Inkscape and developed a set of scripts to automate the build and had everything in a very organized Git repo.