If you boot from installation media like a USB stick or a DVD, then you can only do an install that wipes out your data. There is no option to keep it - with the caveat that you could choose to install on a separate partition and not actually wipe you your old files. Those files would still be present after the install but none of the programs would be installed. However it would be quite simple to go back and move all your pictures and other documents from the old to the new location, for example.
If you boot from the existing operating system and perform an upgrade, then you are given the option of a fresh install which would wipe out your files, or an upgrade that maintains old applications and settings. If you choose this, you might get a message that some applications are not compatible.
You should be aware that Windows will do the best job it can to perform the upgrade without affecting any applications, but some applications might not work exactly the same. There are literally millions of applications out there and the chances that nothing will go wrong when you replace the operating system are low. If you have issues with an app, it often helps to update it to the newest version, or reinstall the old version again. Sometimes you might just need to tweak some of the settings.
If you perform an upgrade (keeping old files) then your old system files are moved to a “Windows.old” directory and replaced with newer ones. As long as you keep the Windows.old directory, you can revert back to the older operating system version later. If everything is fine, you can delete the Windows.old directory to free up disk space. To delete the Windows.old directory, you need to perform a disk cleanup, which is an option you get when you right-click the disk drive in file explorer and select properties. This is also where you would restore the old operating system.
There are also other methods that can be used to upgrade the operating system, such as back up your data to a USB stick or other hard drive, then performing a clean install, then restoring your data from the backup location. Several third-party applications are sold that have this capability, and Microsoft provides tools like DISM that can do it for free.
It will show an option to Keep Windows Settings,personal files & Apps while upgrading, you can keep your files.
When you go through the installation process you can choose to keep all your files or keep nothing, it really is up to you. If you're upgrading from Windows 8.1 or Windows 8 you can keep Windows settings, personal files, and most apps. From Windows 7 you can keep Windows settings, personal files, and most apps. But if you previously ran Windows Vista you must perform a clean install and can keep NOTHING. Sorry, but Microsoft doesn't like Vista anymore. Much like everybody else.
Things to keep in mind
When you go through the installation process you can choose to keep all your files or keep nothing, it really is up to you. If you're upgrading from Windows 8.1 or Windows 8 you can keep Windows settings, personal files, and most apps. From Windows 7 you can keep Windows settings, personal files, and most apps. But if you previously ran Windows Vista you must perform a clean install and can keep NOTHING. Sorry, but Microsoft doesn't like Vista anymore. Much like everybody else.
Things to keep in mind
Unexpected PC crashes could damage or even delete your files, so you should back up everything. You can backup with Best free backup software for Windows 10, Windows 8.1, Windows 8, Windows 7, etc.
Some printers and other hardware might not work, and some software might not install or work correctly, including antivirus or security programs. You might also have trouble connecting to home or corporate networks. Some installed apps might not yet work as expected or might not be available in your country or region.
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