Yes, you can transfer the data, but the best and recommended way to transfer files from a Windows version to the other is doing it manually. The manual mode might be very troublesome, but it will give you maximum functionality and compatibility for applications.
For example, if you transfer the settings and files of the same app from one Windows version to the other, then you should expect errors because although apps are the same, Windows will handle them differently even on the same Windows versions.
For browsers, synchronize the data with an online account and then log-in on the other one. For custom files, share them over the network . Applications need to be installed manually to avoid errors.
