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Ok for those of you looking to find a way to move or migrate your email over to Mac Outlook 2016 from Mac Mail. Here's a real simple method.
Configure Apple Mail/Calendar for Office 365. Open up the Mac Mail client; If you've opened Mac Mail before, please navigate to Mail - Preferences - Accounts. If you have not, skip to step 3. Once on the accounts page, click the Plus button in the bottom left to add a new account. On the following page it will also ask for your account.
Let's assume that you have been using Mac email and your email was setup as a pop or IMAP account. Now you want to switch your email account over to office 365 or Exchange environment and start using Outlook for Mac 2016. So you'll have to migrate your mail over to Outlook for Mac.
Super easy...
1) In your Mac email app, setup another email account but select 'Exchange' as the email configuration. Then enter your email address. (even if it's the same one that you already have setup as a pop or IAMP account)
2) Now you have you should have two email accounts configured in your mac email. The old email account (pop or IMAP) and one that will say Exchange.
3) Go to your old email account in mac mail and select ALL emails then drag them over to the folder called 'Exchange.
4) Now all your email from your old account will sync to the new email account called Exchange. That's moving all your emails from your pop or IMAP account that are stored on your notebook to Office 365 or exchange (in the cloud)
5) Open Outlook for Mac and configure your email address there and it will start pulling down all your emails you just dragged over.
Now you have your emails from your Mac email to your Mac for Outlook. Also be sure to copy over your sent and deleted items as well.
Hope that was helpful...this is what I was looking for but couldn't find and finally figured out how to do it.
MacBook Pro, OS X El Capitan (10.11.5)
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-->Import or copy email from Gmail or another email provider to Office 365.
Want help with this?Contact Office 365 for business support .
You need to use a version of Outlook that is installed on your desktop for this task. Outlook is included in most Office 365 plans.
Import from Gmail
Follow these steps to import email, contacts, and calendar from Gmail into Outlook with Office 365:
Import from Outlook (desktop)
Follow these steps to export email, contacts and calendars from Outlook to a .pst file, and then import that file to Outlook with Office 365:
If you just want contacts, follow these steps:
To start the process, open Outlook and choose File > Open & Export > Import/Export.
See other email accounts in Outlook
Just want to see your email from another provider (like Gmail, Yahoo, or Live.com) in Outlook? No need to import or migrate. You can set up Outlook or Outlook Web App so you can access your other accounts from the same place as your Office 365 mailbox and send, receive, and read email sent to those accounts.
Outlook (desktop)
Add an account, such as your private Gmail account, to Outlook.
- Open Outlook, then go to File > Add account.
Need more detailed steps? See Add an account.
Multiple mailboxes: Admins can bulk import email, contacts, and calendars to Office 365
Depending on your source email system, you can choose from several bulk migration methods. Read Ways to migrate multiple email accounts to Office 365 to decide which method works for you.