As a Mac user, I’ve watched Windows grow up from the outside. There was so much wrong with Windows 3.1 / 3.11 that it was hard for us to believe that PC users considered it to be superior to the Mac. (On the other hand, before Windows, PC users had often considered DOS to be superior to the Mac.) Back then (in case it predates your PC experience or you’ve managed to forget), there was no icon on your desktop representing the place your files are at. In fact, since you also could not put programs or files or shortcuts to programs or files on your desktop, it would be fair to say that there was no desktop. What there was instead was a sort of bland useless screen on top of which windows would open if you selected them from a menu. The windows available in the menu – called “Program Groups” – were sort of little launchpad things for starting up programs in various categories (Games, Accessories, Microsoft Office, etc). These were not folder windows, where you were looking at actual files, so the only thing you could do once you’d opened one of these windows was launch one of the programs whose icon was in that program group. In other words, launching a program required opening a window from a menu, then double-clicking the program icon within the window. If you wanted to launch a second program, you would minimize the first one and find yourself staring at the open program group window, which you have no use for now that you’ve launched its program, so you’d close it and go the menu and pick another and then its window would open and you’d repeat the process.
File management was accomplished in a special program called File Manager, and once inside it you would discover that the hierarchy of actual files and folders (and filenames, including program file names) bore no relationship, really, to the set of categories in the Program Manager. In File Manager, icons were all pretty much generic little white things except for programs which, if I recall correctly, were pretty much generic little blue things. Despite its lack of decor, though, you could run everything from File Manager if you wanted, going into the folder containing the actual program you wanted to launch and then double-clicking the program file itself to launch the program. Most of us Mac users wondered why PC users ever bothered with the program manager and why they didn’t make the File Manager their “shell”. Maybe some did. Anyway, the File Manager, while not the dumbed-down yet user-hostile piece of shit that was Program Manager, would not remember the placement of icons if you dragged them around, so you could not organize your folders. You could do decent list views, but the next time you opened the folder it would not remember your viewing preferences and you’d have to set them again. There was another way to view your files, which was the tree, and the tree was cool, actually, a hierarchical menu of your drive with little + signs to expand or - signs to hide the contents of any folder. (Directory, they called them back then). The GUI to the tree view needed work, though – on a big hard drive with lots of subsubsubsubfolders it was very difficult to follow those vertical lines on the right and figure out where the heck you really were in the overall scheme of things.
Windows 95 was when Windows grew up, interface-wise. Windows 95 shitcanned the Program Manager and gave you a Desktop (a real one, you can even put files and programs there, not just shortcuts to them), a launching menu (the Start Menu), put a decent GUI onto file management and incorporated the hierarchy of files into the Desktop motif (the “My Computer” icon and within it the icons of the various drives), and cleaned up the messy window interface with elements borrowed from Unix X-Window and Apple’s Macintosh. Windows hasn’t really changed the fundamental GUI since. The XP universe is just the Windows 95 world with more orange and bigger text 
Most idiotic remaining characteristics of Windows?
a) The program window. All document windows of a given program are enclosed by a program window, which means you can’t put a Dreamweaver project document between one word document (resized long and skinny and placed along your left screen-edge) and another (small and off to the right) and intersperse your Dreamweaver palettes and additional windows above and on the 2nd monitor and so forth. Instead, every bloody program is opaque to the documents of another.
b) Old-fashionedy file path based file identification system + the registry. An ideal OS doesn’t care if you rename folders, rename files (including application files), move them to another location (including another drive) or even boot from another bootable volume – it should still be able to launch and run the program. Not all of Macintosh reaches that ideal (some programs demand that their custom extensions be present under MacOS 8/9, and under MacOS X a few insist on being in the Applications folder of the startup drive, not to mention the native Unix binaries that won’t run if you move or rename anything that they need to reference) but the batting average is good. On Windows it’s pretty horrid. So under Windows you end up with a buttugly hodgepodge of foldernames and whatnot that you can’t organize because you can’t move or rename anything without breaking something. (Under the MacOS, we end up with a buttugly hodgepodge of foldernames and whatnot which are entirely of our own design ;))
But the PC has come a long way, baby. From DOS to Windows 3.x to Windows 95+, Microsoft has covered a lot of territory, user-experiencewise. I wouldn’t want to have to use it, but I acknowledge that the MS OS enduser experience is a serious and legitimate alternative to the MacOS enduser experience, with some good points (Open/Save/Save As dialog box access to files and file functions for example) amidst the bad points, and I think they deserve acknowledgment for that.