20 years ago I was a teenager. My family wasn't rich growing up. By that point I'd owned a second hand Commodore 64 I bought for $75 through the classified ads, an IBM PC XT I bought from a consignment shop, and a 386 I built from pieces I bought second hand from a friend who was upgrading to a Pentium system. Around this time 20 years ago I was finishing up an internship I had in between my junior and senior years of high school that I had because I spent some time on BBSes and the guy thought I would enjoy learning to develop software with them. During the summer I used a 486 DX2 system with Windows 3.1. That was my fist real exposure to Windows.
There was a local trade mag for computers that they gave away free every month at news stands. I always enjoyed reading them and there were a lot of articles on Win 95. No one I knew had it or got it over the next year.
The following year when I was getting ready for college, one of the thing we had to buy was a modern computer to meet the requirements for my engineering program. It was built by a local shop and they offered DOS 6.22 / Win 3.1 or Windows 95. I remember being hesitant about 95, but decided to go for it since it was newer and I knew newer aoftware was designed for it.
That design really opened up computing to a lot of people. Having a single place to go to Start any program was a great idea. Before you had to know what directory to look in or where in Program Manager an icon was. All my non technical friends in college had no problem with it. With Windows 3.1 they would struggle and if they had to drop to DOS they were mostly lost. If you want to know what's running, it's right there on the task bar.
I've used various versions of Windows and Linux over the years, but I think the biggest legacy is the start button and task bar. They pretty much define how most people interact with the desktop. The Windows 8 UI debacle and the shift back to a start menu / having Modern apps on the task bar shows that it's how users have come to expect to interact with a desktop system.