When I worked at LEVEL Studios (which became Rosetta) in the early 2010s, we had a whole group dedicated to icon design. It was small but incredibly talented and led by Jon Delman, a master of this craft. And yes, Jon and team designed icons for Apple.

Those glory days are long gone and the icons coming out of Cupertino these days are pedestrian, to put it gently. The best observation about Apple’s icon decline comes from Héliographe, via John Gruber:

If you put the Apple icons in reverse it looks like the portfolio of someone getting really really good at icon design.

Posted by @heliographe.studio on Threads

Seven Pages icons from newest to oldest, each one more artistically interesting than the last. The original is exquisite. The current one is a squircle with a pen on it.

This is even more cringe-inducing when you keep in mind something Gruber recalls from a product briefing with Jony Ive years ago:

Apple didn’t change things just for the sake of changing them. That Apple was insistent on only changing things if the change made things better. And that this was difficult, at times, because the urge to do something that looks new and different is strong, especially in tech.

Apple’s hardware team still operates this way. An M5 MacBook Pro looks like an M1 MacBook Pro. An Apple Watch Series 11 is hard to distinguish from a Series 0. These designs don’t change because they’re excellent.

The software team lost that discipline somewhere. Gruber again:

I know a lot of talented UI designers and a lot of insightful UI critics. All of them agree that MacOS’s UI has gotten drastically worse over the last 10 years, in ways that seem so obviously worse that it boggles the mind how it happened.

The icons are just the most visible symptom. The confidence to not change something—to trust that the current design is still the best design—requires knowing the difference between familiarity and complacency. Somewhere along the way, Apple’s software designers stopped being able to tell.