My grandmother's computer is an old Debian box with nothing more than `ly` (as a DM), xfce, Chicago95, and Firefox. She loves it, though I made a ton of tweaks here and there to make it easier for her to use (specifically a ton of website launchers on her desktop). She got lost in regards to how to use her computer back in the XP>8 transition so it was great to be able to bring her back to that style of desktop and have the system be easier to fix than Windows 8 or 10.

I've used Memphis98 (similar to Chicago95) since it came out. Although just as a GTK-theme, not the entire desktop. Window manager is FVWM and taskbar/panel/session-manager is LXQt, so it's a bit of a Franken-desktop :)

For Qt-apps I use the "Windows" style so they fit together nicely.

Comparing Memphis and Chicago, there are some layout-bugs in Memphis, but I feel like it's overall a bit better balanced than Chicago.

I think all new themes are too bright and flat, Windows 9X was perfect (at least in that regard).

I ran it for most of 2020 before moving to KDE. I hadn't looked at the project recently until today and saw that it now has 'Chicago95 Plus! A tool to preview and install Windows 95/98/ME/XP themes'.. I'm going to have to try it that out. Of course, I'm probably an outlier in that I love the visual design of user interfaces from that bygone era.

I’ve used chicago95 as a daily driver for a few years now. It’s simple, high contrast, gets out of my way and lets me work.

I used XFCE with this exact theme for a few months and I loved it. The only thing I didn't like was that the light gray top "outline part" of the window decoration doesn't disappear when you maximize a window. I never figured out how to fix that.