Hi Kara,
Thanks for reaching out! Our Event Aggregator tool can perform automatic imports from a number of sources, including iCal/ICS feeds, Google Calendar, and Facebook. If your version of Outlook is able to export to one of the listed formats, you should have no issues setting up automatic imports with Aggregator! If you’re not sure, I’d suggest referring to the documentation for your version of Outlook to see what options are available for exports and syncing.
I hope that helps to get you started here! Let me know if I can answer any other questions for you. Cheers, and thanks again!