O&H, is that 'real' Outlook as in the Outlook part of Office, or that standalone p.o.s. Outlook.com which seems to be the latest incarnation of the useless Windows Live Mail. Or perhaps it's the latest new name for Hotmail?
If the latter, I would recommend NOT trying to upload any address book. I had a few addresses saved on Hotmail a while ago and someone hacked them, then spammed everyone on the list. It took days to recover Hotmail....
Now I use Outlook 2007 - but my new back-up laptop has Outlook 2016 which is even more complicated and user-unfriendly than Outlook 2007. But it does actually open my old archived .eml files from the much simpler (and more user-friendly) Outlook Express, something which Outlook 2007 won't.
I also access my Hotmail account through adding it as another e-mail account in Outlook 2006 / 2017.