That definitely is strange! I am using OS 10.11.6 on my mid 2013 13" macBook Air, along with Outlook 2016 for my EMail needs, and even after updating Outlook 2016 to V15.28 the other day, I am not having the issue you are. In fact, I tried to drag the lower right corner of Outlook 2016 over the dock, and it would not let me!
Do you happen to remember any updates you did? I tend to install my updates on my own, especially ones from Apple. If you let some app install an update automatically, that could be the culprit. I did, though, let 1Password do an "update" in place the other day (I later downloaded the updater myself), and did not have any issues.
Maybe you could try installing the last Combo Updater for Yosemite, OS 10.10.5. You can get it from here:
https://support.apple.com/kb/dl1832?locale=en_US
That might do the trick for you!
Hope it helps. If you do try it, please let us know what results you see.
One other thing I for got to mention is that if this does the trick, you should make a backup of it, as it would be a "clean" one. Also, what software do you use for your backups?