New
#11
No, you can't. You can however upgrade Vista to Windows 7 keeping installed files and apps, and from there you could upgrade to Windows 10. In order to upgrade from W7 to W10 the W7 has to be activated, so you'd need a legitimate W7 key. The activated W7 would then entitle you to an activated W10.
In fact, you can upgrade XP to Vista, and I have done the whole round trip from XP to W10 in a VM to retain use of some licenced software installed on an old XP machine of mine. The PC died long ago, but I still had the HDD and restored a Macrium image of it to a VM.