Seems like some progress has been made because the oldest style here is as recent as Win95.

For a long time, the "Install Font" dialog was unchanged from Windows 3.0, with a tiny little folder tree view meant for 8.3 character file names and a drive picker button...

Some googling reveals they cleaned these up around 2015: https://arstechnica.com/information-technology/2015/09/windo...