Support for importing from or synchronizing with iCal is not yet available in Outlook 2016 for Mac.
If you would like to request this feature, visit the Outlook Feedback UserVoice to leave your suggestion. The Outlook team is actively monitoring this forum.
Do any of the following:
Import Apple iCal events and to-do items
Outlook can import events and to-do items from iCal. In Outlook, the to-do items appear as tasks.
In iCal, on the File menu, point to Export, and then click Export.
Note: Outlook can only import iCal events that are saved in the Export (.ics) format. Outlook can't import events saved in the iCal Archive (.icbu) format.
In the Save As box, type a name for the exported file.
On the Where pop-up menu, select a location on your hard disk to save the file, and then click Export.
In Outlook for Mac, at the bottom of the navigation pane, click Calendar .
In the Finder, locate the .ics file, and drag the .ics file to the Outlook Calendar grid or list.
Import Apple Address Book contacts
You can export contacts from the Apple Address Book as a vCard, and then drag the vCard file into Outlook to import your contacts.
Tip: As an alternative to importing contacts from the Apple Address Book, you can turn on Sync Services for your Outlook contacts. Turning on Sync Services syncs your Outlook contacts with the Apple Address Book, MobileMe, and other applications or devices that you set up in Apple iSync.
In the Apple Address Book, select the contacts that you want to export, and then drag the selection to the desktop.
The contacts are saved as a vCard file that contains all the contacts.
In Outlook for Mac, at the bottom of the navigation pane, click Contacts .
Drag the vCard file from the desktop to the Contacts item list.
Note: Contact groups in the Apple Address Book are converted to categories in Outlook.