With the ability to install straight from a repository the Chicago95 theme, I honestly feel there is no more need to use Windows 10 with Classic Theme. I've found that Debian can just about run all of the software that I was using on Windows quite easily.
Anyone else using Chicago95 on a Debian/Ubuntu based Linux system?
Yep, I am using XFCE as well. Honestly, I'm this close to just eliminating my dual boot of Windows, which has really just started to break down lately. If you're really curious, the guy who made this theme also created something called Chicago95 Plus! which allows you to run a python script at a MSStyles Theme and converts the theme into the Chicago95 theme for you to use. It's not perfect, but it's well-written. Then I just continue to use Pale Moon and the Moonscape script and voila, I've got just as much of a Windows95 theme on a much more stable system.