Mac - Migrating from Outlook 2011 to 2016
Outlook 2016 can import all settings from Outlook 2011 on an existing system.
1) Go to the Applications folder (Click on the desktop, and then Finder/Go/Applications from the top toolbar)
2) Drag the icons for all the Office 2016 applications to the dock at the bottom of the page, one by one. This will populate the dock with shortcuts the applications.
3) Remove the older Office 2011 icons from the Dock by clicking on them and dragging them off the dock. Do not use Office 2011 after this point, but use 2016 instead.
4) Open Outlook, and ignore any prompts to enter credentials or username. Cancel these prompts
5) Instead, go to File and then Import from the top toolbar in Outlook
6) Follow the instructions to import from Office 2011. When prompted, choose the "Main Identity" from Outlook 2011.
7) This will take a while depending on how much data you have.
8) Once this has been done and all Office 2016 apps have been checked, the folder for Office 2011 may be trashed form the Applications directory, removing Office 2011.