Using older versions of Outlook for Mac for personal email and calendar
Here's a quick fix that worked for me (from this article https://www.howtoisolve.com/exchange-calendar-not-syncing-in-macos/)
- Click Outlook > Preferences.
- Go to Accounts: In the Preferences window, pick the Accounts option.
- Choose your account: On the left side, select any account that's not syncing.
- Reset the account:
- Click More Options (the circled three dots in the left panel), then hit Reset Account.
- Restart Outlook:
- You'll see a message saying you need to restart Outlook for the reset to happen. Just click Restart Now, and you're good to go!
In my case Outlook Calendar synced again properly with the Apple Calendar app.