Windows 95 — How Does it Look Today?

Dmitrii Eliuseev
10 min readApr 2, 2021

Windows 95 was the “next-generation” OS from Microsoft: redesigned UI, long file names support, 32-bit apps and many other changes. Some of Windows 95 components are still in use today. How does it look? Let’s test it and figure it out.

I was not going to make a review of Windows 95, it was actually not so many years ago. But once I saw the video, something like “Teens react to Windows 95”, and it’s become clear that there are already not only teens but a whole new generation of 20–30 years old adults who never used Windows 95 in their life or were too young to actually remember it. And anyway, Windows 95 was a great milestone in the computer's history, the great improvement from Windows 3.1 to a new system, parts of which we are using still now.


It can be tricky to install Windows 95 to a modern PC, but it’s actually not needed—Windows 95 can run on the virtual machine. Windows 3.1 is running perfectly in DOSBox, it’s a nice and lightweight emulator that even does not require installation and can be executed from any folder. But DOSBox officially does not support Windows, in theory, it can be possible but it’s much easier to use a fully-fledged virtual machine. I’ve used Oracle VirtualBox, which is free and can be installed on any modern PC.

To install Windows 95 we need to find 2 files: bootable floppy disk image and Windows 95 CD image, they can easily be found online. I also created a new virtual machine with 128MB of RAM and 2GB HDD:

Oracle VirtualBox Settings

First, we need to create a disk partition using the fdisk command (it will be our drive “C”), format this disk and copy installation files from Windows 95 CD to this disk (for an unknown reason, the installer cannot find some files when it’s running from CD image directly).

Want to read this story later? Save it in Journal.

Now we are ready to start:

Windows 95 Installer



Dmitrii Eliuseev

Python/IoT developer and data engineer, data science and electronics enthusiast