Hm. Hard to say. I do like WfW 3.11, but somehow plain Windows 3.1 too.
Vanilla Windows 3.1 can still run on good old 80286 in pure 16-Bit and also within other environments, such as DESQView/X.
Then there's OS/2, which I do have a soft spot, too.
And then Windows 2.03 which I've used to use as a runtime for playing Klotz when I was little.
When it comes to DOS, I did like MS-DOS 6.20 the most. It's what I had used in my 'childhood', too.
However, I'm nolonger using it. I keep it as a memento, rather and use MS-DOS 6.22 instead. ;)
PC-DOS 3.30 is also a nostalgic piece of software to me. I've used it with Windows 2.03, too.
That being said, other DOSes like Novell DOS 7, DOS Plus 1.2 or PC-MOS/386 are interesting, too.
Novell DOS perhaps was the most advanced DOS of the 90s, with all of its networking stuff and sophisticated memory managment.
Unfortunately, a GUI was missing (GEM 3 or ViewMAX).
It makes for a nice partner to WfW 3.11 or GeoWorks Ensemble.
That's because Novell DOS has support for peer-to-peer networking, too.
GeoWorks can use both the TaskMAX and TaskMGR of DR DOS/NV DOS (there's that carousell icon in GEOS preferences).
Then there's Windows 98SE, which strangely I have gotten a soft spot for in the past years.
More than as for Windows 95, which is strange, because I knew Windows 95 since it was being released.
I suppose it's because that Windows 98SE marks the end of 20th century.
The GUI elements, concepts and the language used are a reminescence of the outgoing old millennium.
Also, Windows 98SE seemed to had a friendlier face than Windows 95 and provided a helping hand through various assistants.
Windows 95 feels unpolished in retrospect.
That being said, Windows 95 was the big brother to Windows 3.1 and it had a lot of contacts to the passing 16-Bit era.
In the days of Windows 95, new 16-Bit applications had still being made using 16-Bit compilers and IDEs.
Some even checked for "3.95" version via Win16 API and used features not available on real Windows 3.1.
Then there's Windows XP, which allowed for a lot of customization and personalization. It was the first real OS to many people.
To me, Windows XP has become like an old worn sofa over the years.
It's dated, half broken but still feels like home more than all of its successors.
Someone could say it has developed a certain charme or personality over the many years.
Best Sci-Fi OS/Best GUI:
LCARS.
There's LCARS24 for DOS, which is actually functional.
It's not the only DOS sci-fi GUI, though. There's a jukebox and a couple of GUIs, too.
PS: If non-PC OSes do also count..
🌈Rainbow TOS (Atari TOS 1.04), Amiga OS 1.3 (Kick 1.3/WB 1.3), GEOS+The Final Cartridge III
68k Macintosh: Mac System 7.x and A/UX
PPC Macintosh: Mac OS 9.x and Mac OS X with Aqua (10.0-10.4)
Intel Macintosh: OS X 10.6 Snow Leopard ("Snowy")
"Time, it seems, doesn't flow. For some it's fast, for some it's slow.
In what to one race is no time at all, another race can rise and fall..." - The Minstrel
//My video channel//