I had the same issue of settings not loading. Microsoft's support gave me the solution below, which worked for me:
- close Outlook
- type "command prompt" on the Windows search bar
- right-click on the "command prompt" app that shows up, choose "run as administrator"
- within the command prompt, type olk.exe --clearLocalState, then hit enter
- open Outlook
The steps above effectively removed all accounts I had in Outlook while keeping all my settings intact. So all I had to do was re-add the accounts and go on to use Outlook as before.
Note that in my case I was having the "settings not loading" problem due to having an account added to Outlook that I no longer had access to. Depending on the source of your problem, the solution above may or may not work.