I'd say it looks like someone getting decent at icon design, then getting worse -- in either direction. Both the extreme left and right are crap icons: one, too little information; the other too much. Neither does what an icon should do.
None of them are truly good. They all look like someone trying to make a mark and fulfill the vision of a 'design school' instead of someone trying to make a usable affordance.
None. Ever.
Icons are a tool.
They are a mnemonic place to click to perform a repeatable function.
An icon cannot be great; just as a hammer, a zipper, a doorknob, or a roll of toilet paper cannot be great.
They can be functional, or not, or somewhere in between. Functional is good, there is no great. Below functional is bad.
The best are functional, consistent, and predictable. They still aren't great, because an icon can't be great...it either fits or it doesn't.
If you change it, there needs to be a better reason than 'pretty' or 'we changed our branding'.
Forcing users to adapt to changing style guides is a great way to piss off users.
Too many people went to art and design schools and decided that icons needed to be "art" -- instead of tools.
I went to those schools as well. Most of my classmates never got the punchline:
Form should always follow function.
@johntimaeus @heliographe_studio
“None of them are truly good.”
“What’s an example of an icon you like?”
“I hate icons.”
Fantastic!
@kylehalevi @johntimaeus @heliographe_studio
I agree: the best is the one in the middle.
The orange ones are bland and lacking contrast, the one in the left is hard to understand. The ones on the right are too literal.
The middle one is clear, has excellent contrast, and it is nice to see.
Apple traditionally has had a tendency to fall in the skeuomorphist pitfall. Icons must be as recognizable as traffic signs, and should be beautiful and fit with the overall design. But being subtle is not one of Apple's design strengths.
I think other desktop OSs have had it better. Ubuntu default icons have a nice balance of aesthetics and function. Windows icons change so much that you can love one version and hate the next; but they usually keep them very functional.