What type of email account do you have configured in Outlook? POP, IMAP, Outlook.com, or Microsoft Exchange?
Only Outlook.com and Microsoft 365 Exchange accounts sync calendar & contacts to classic Outlook. IMAP and POP sync email only. You need to use a 3rd party sync tool to sync calendar & contacts - iCloud add-in is free for iCloud account, or gSyncit, which is not free but sync most calendar & contact providers (including iCloud, but is better than the iCloud add-in in my opinion.)