Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi Matt,
First of all, we will submit the feedback to our relevant team about your original concern.
About “don’t have smile icon in Outlook client”, I already tested from my side, we can view the smile icon on the upper right corner of the Outlook client when we download the Office application via Business Premium plan. But, when we download the Office application via Enterprise E3 or Enterprise E5 plan, we cannot view the smile icon on the upper right corner.
Please also try the short key “Ctrl+Alt+7” & “Ctrl+Alt+8 " to open the feedback page in Outlook client.
Generally, out of the box version can view the smiley icon on the Outlook client, you cannot view the smiley icon may due to customize of your Outlook client.
In this situation, I would like to confirm you downloaded the Office application via which Office 365 Plan and the detailed version of your Outlook client.
Thanks,
Poppy