I think this spectrum shows the issues with that though. Take the last one, the pen pot. You truly have to _learn_ what that means. Pen pots aren't a thing that most people are familiar with (I've never used one, I don't think my parents generation did mostly either), and there's little explanation of what it is.

Move up just one previous, and you've got a good looking illustration still, the pen and paper, but now a) everyone knows what a pen and paper look like, b) it literally says the name of the app, and c) the yellow colour scheme distinguishes it well when scanning many icons. It's clearly more accessible to new users, existing users, young and old users, and in terms of illustration quality, seems pretty subjective as to whether it's better or worse than the last one.

I’m not convinced the pen pot needs any more learning than anything else. Even the ones with the paper - is it a word processor, emailing tool, something about newsletters? Maybe a PDF or markup tool? Or a layout tool for print media? Or just a signature tool?

At some point, the user has to find out, in the same manner they find out about the pen pot.

I think users could easily associate the “pen and poison potion” with word processing for years until someone says “click on the pen and ink” and then they have a lightbulb moment.

I think we went from icons being “visually distinct” to “visually descriptive” to “visually uniform”. Personally I prefer the visually distinct. I’m not convinced we gained some massive leap forward in usability moving away from it; I know I struggle substantially more to find an app or tab that I’m looking for nowadays than when I first got a Mac.

> Pen pots aren't a thing that most people are familiar with

Personally, no. Cognitively? We've been seeing quills and ink in children's stories for centuries. One doesn't have to have used a bubble level to get the analogy in the iOS Level app.

> pen and paper, but now a) everyone knows what a pen and paper look like

A quill and ink are conventionally portrayed in relation to writing. A pen and paper could refer to e.g. sketching.

I'm obviously nitpicking. But I reject the notion that we have to oversimplify to the degree you're suggesting.

> it literally says the name of the app

The OS does this almost everywhere apps exist. Putting the name in the logo is superfluous.

I think that is the flawed conscious reason for these icons getting excessively oversimplified and minimalistic. And why the Save floppies were replaced with inconsistent crap. And some higher-up at Apple's severe untreated OCD is the reason for the excessive uniformity (squircle jail, one saturated dominant color, the geometric "grid system" they keep bragging about at keynotes). Look at old Launchpad screenshots from OS X Lion and you'll see what drove that guy nuts and made him ruin every icon.

I showed this timeline to non-technical people around me and they prefer... the original pen pot.

>a) everyone knows what a pen and paper look like, b) it literally says the name of the app

c) Pages plays for the Dodgers

aaahhh! i get it, it's a sports autographs app!