Don't know if Outlook works. That part was the one part of Office that always caused me issues in Wine (but, frankly, I haven't tried it in years). Word, Excel, PPT -- all worked great otherwise. (small tip: if I disabled compositing in my window manager, then the translucent selection drag box in PPT turned black, making it impossible to see what I was selecting.)
Also, there's a very simple extension for OWA in the chrome app store; it just tricks OWA into thinking you're running Chrome on Windows instead of Linux (where microsoft subjects you to the ancient version instead). I know the author pretty well ;) However, I haven't been forced into running OWA or connecting to Exchange at all, so it might have bitrotted or not be needed anymore:
Also, there's a very simple extension for OWA in the chrome app store; it just tricks OWA into thinking you're running Chrome on Windows instead of Linux (where microsoft subjects you to the ancient version instead). I know the author pretty well ;) However, I haven't been forced into running OWA or connecting to Exchange at all, so it might have bitrotted or not be needed anymore:
https://chrome.google.com/webstore/detail/owa-user-agent/bbc...