Yes it can work- and if you're looking for an everyday bag the weekender is obviously out of the question, and to me the work is a bit large as well. Get the size you need- the moto isn't a feminine bag. I also believe in wearing what the hell you want.
Got the work a couple of months back (did a reveal here) and since then I have been craving for a bbag with a strap. Almost bought a part time 2010? anthra (bluish undertone when compared to black) with rh, but decided against it because what I really wanted was a pt in canard with rh and they only got SGH that was a bit too much for me at the time. I must admit I am now having second thoughts... and that I should have bought the pt in canard with SGH! (yes I'm a man)
I've tried a Evergreen rh Pt at the boutique before and it really looks quite good especially with the strap. But I find it kinda shallow and was afraid that things may fall out of it as I usually use my bals unzipped.
Even with my Work and WE, I've had stuffs falling out of them cause they slouch so much! Or maybe it's just that I'm clumsy. Lol
Anyway you should get whichever that's most suited to your lifestyle and usage.