*correction:

I like 1998 and 2000 icons the most. 2000 in particular is so stylish.
Look at this whacky 2006 shit Sorry for the reddit link
Bunch of bangers 🤷
gotta say XP and 7 ones are the coolest.
2006 sure was a whacky time to be alive. That was the year of borat and everything was whacky. Did you the last telegram was sent in 2006. What do you remember about 2006?
I assume that last one is some sort of AI app.
Yes, copilot
2026 should look like a garbage can with the windows logo in it
I like 95-00. That’s also the period in time in which I liked Windows, so there’s certainly a correlation there.
1995 and 2015 looking go tho
I’m partial to 1998. That’s my favorite one.
Same, maybe a bit 2000 also. They give this nostalgic feeling. I think it is the high quality pixel art-style that reminds me of simpler times.
never used anything under windows 8.1 in my entire life - 2000 and 2001 are my favourites
It peaked in 2006
2006 is actually close to MacOS’ trash icons, which indeed always looked way better.

I think for the Mac icons here I like the 2001 variant.
Yeah, that was what I’m most familiar with, and it felt neat as heck. 2014 is probably part of overall change away from Jobs’ skeuomorphism to glass texture that Jony Ive likes.
'98 is best.
2015 is second best.
Agree on 1998, disagree on second best.
1995 was second best.
Pixel art has my pixel heart.
2001 for me. It was colourful and round, didn’t feel like a boring square box. While XP wasn’t always the most stable, it was a good OS.
just like Windows itself ( correction : Windows peaked 2009 - 2012 )
Seriously though, the thought of an llm running on a server interacting with my files is one of the most frightening things I can imagine happening to anyone
I don’t want to sound like I support ANYTHING about Windows 11, because I don’t.
That being said, take your clothes off, I’ll tie you to this torture rack I keep in my basement, and I’ll get you to reevaluate what fear really means.
Hey, are you ticklish?
deleted by creator
My brother in christ, perfometh a websearch to look for the meaning of the word “hyperbole”.
Who hurt you
At least the polar bear won’t lie to me about my search results.
The 2025 trash icon no longer looks like a trash can. It’s no longer intuitive. At the same time, I don’t actually keep one on my desktop, so meh.
Isn’t it the copilot icon or have I been taken to an alternative universe?
If it is, then I failed to get the joke.
Yeah, there should be a whoosh somewhere above you.
And yet you still managed to accidentally make a pretty funny joke. Win/win.
2001 is my bae
2006 sick 3D
That’s the recycle bin. Mac OS has trash.
The former icon designer in me twitches when I see Linux distros that have Recycle Bin icon labeled as “Trash.”
Windows is the trash














