I haven't tried this[0], just found it through a quick search but it looks like it should be possible to get a CalDAV interface to Outlook.

Both calcurse and remind support CalDAV sync (experimental in the case of calcurse). calcure does not seem to support it; just opened an issue for it.

[0]: https://caldavsynchronizer.org/

EDIT: Several mentions of Outlook on software listed under https://devguide.calconnect.org/CalDAV/introduction/, maybe there is something that works for you