This will probably work:
Go to FILE menu, then OPTIONS (probably toward the bottom).
Then choose “Trust Center.”
Then go to “Automatic Download”
Then you will see checkboxes for whether the pictures display.
Uncheck the “Do not download” (etc) checkbox or whatever is showing there.
It is not considered very secure to display pictures because they can track you, and it is another route to hack you. I intentionally do NOT have pictures showing in e-mails. So yours is set right probably. If your outlook is controlled by your organization (like work) then this setting might not be changeable.
If you leave it to not show images, there is probably a banner or link of button at the top of individual messages that will show images in that message.
You will also have to show the image in HTML and not in TEXT of the images will not show (unless they are attachments).
You also can probably right-click the message and there might be a menu with options to show in HTML and/or show images.
Hope this helps.
Happy New Year
I tried that too, same result. You know what’s weird, is that a month or so ago, I only had the problem with Outlook 2010. Outlook 2018 worked just fine, but now both versions have the same problem. I tweaked Trust Center to no avail.