Transferring hdd content to & from a usb caddy

Hi, I would like to know if anyone can tell me if I can take a typical 2.5" sata laptop hdd that has windows xp along with some software, and transfer my data via a usb caddy Then transfer all the software content (minus the os) via usb caddy to my newer windows 8.1 system? Thank you for any solutions.
 
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