For everyone wondering which versions of Outlook require and don't require App Passwords, here's a list of what's needed for which versions:
For Gmail POP, it will be necessary to create an App Password and use that password in place of your regular password when adding the account to all versions of Outlook. The reason for this is that Microsoft only updated the IMAP protocol to support OAuth, Gmail's requirement for an email app to be listed as "Secure"
For Outlook 2016 and earlier it will be necessary to create an App Password for both POP & IMAP accounts.
Outlook 2019 and later support OAuth for Gmail IMAP. With OAuth you only need the regular password. If, however, you have a Gmail POP account, an App Password WILL still be required. It's still a good idea to turn on 2-Step Verification to secure your account but it's not necessary for Outlook 2019+.