(Codeweaver's contributes perhaps the majority of code to Wine 3.0, so Wine 3.0 will also run it well, but they have a terrific product because they allow you to essentially sandbox each Windows app into a different wine "bottle" container with different settings for each, and by providing default settings and switches for most major apps.)
Interesting. Just today, I decided I'd had enough of outlook 365 Web client. Maybe I'll give outlook 2016 and wine 3.0 a try - before I fall back to plain imap etc at work.
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:
https://www.codeweavers.com/compatibility/crossover/microsof...
(Codeweaver's contributes perhaps the majority of code to Wine 3.0, so Wine 3.0 will also run it well, but they have a terrific product because they allow you to essentially sandbox each Windows app into a different wine "bottle" container with different settings for each, and by providing default settings and switches for most major apps.)