Oh hi everyone! So funny to see how my quippy little tweet blew up the last few days on all the platforms (much more than when I share actual things I make, to my great dismay - if you're an artist/photographer, check out my apps & tools: https://heliographe.studio).

There's lots of interesting discussions to be had around what makes a great icon (but social media platforms aren't the places to have those deep conversations). For example the original Mac HIG says that an app icon should:

- clearly represent the document the application creates

- use graphics that convey meaning about what your application does

(https://www.threads.com/@heliographe.studio/post/DTehlciE3wY)

The first point might be a little outdated, as we tend to live in a "post-document" world, especially on mobile. The second is broad enough that it holds up, and under that lens it doesn't seem that an image of a pen/stylus is most appropriate for a word processor app.

By that metric, the Mavericks/Catalina (5th and 6th on the linked image) seem like the strongest icons. The Big Sur (4th) one isn't too bad given the "must fit in a squircle constraints" that came with it, but it starts to feel less like a word processor app icon - it could as easily be an icon for TextEdit/Notes.

The most recent 3 are very hard to defend - the main thing they have going for them is that because they are simpler and monochromatic, they fit more easily within a broader design system/icon family. Even then, the simpler shape doesn't make them more legible - a number of people have told me they thought it was a bandaid at first, or maybe something terminal-related for the orange on black one. The "line" under the pencil (or is it a shadow?) on the most recent one is almost as thick as the pencil itself, and blends with it because gestalt theory.

I agree that the 7th one (original ink bottle) has a few issues that don't necessarily make it the best choice for an icon - but dang, the level of craft that goes into it makes it an instant classic for me. And it does retain a fairly distinct, legible shape that still makes it a solid icon even if the detail gets lost at smaller sizes.

Icons need to be quickly recognizable, but at the same time an icon is not a glyph - and illustrational approach do have their place. Especially on devices with larger screens where they are going to appear quite large in most contexts.

The big elephant in the room with all this is that icons 5/6/7 clearly take more craft skill to execute than icons 1/2/3, and Apple used to be the absolute reference - no debate possible - when it came to these matters. As a long time software designer (and former Apple designer myself through the 2010s, although I was on the hardware interaction design side, and not making icons), it is sad that this is no longer true.

I grew up with Hypercard etc. and always loved the classic icons, like these: https://99percentinvisible.org/article/designed-with-kare-in... Don't suppose you've ever extended the timeline further back? I bet there would be some interesting discussion!