Thanks, all!
DEB, lighter and plainer underneath would probably look good--I would try that.
tr3kkiegrl, you are right, boyfriend chinos (or cords, in this case) are a rumpled kind of look, and I do see your style as more polished. I am not entirely polished--I like a little bit of soft, relaxed, or RATE in an outfit.
texstyle, I had the same thought about the belt. I tried on a sage green/gray one I just got, but then switched to the pewter. To you and AM: the few times I've tried wearing tops untucked with boyfriends, I've immediately switched to at least a semi-tuck. Something about it just hasn't worked on me, to my eye.
unfrumped, interesting thoughts, as always! As it happens, I'm wearing my loafers today, with a tapered pair of chinos. I tried them with oxfords and didn't like the look as well as the loafers. I'll have to experiment more with rolling the pant-legs on my wider boyfriends. I did roll these cords a little bit, but not enough to show any ankle. I agree with you that I would prefer a little more ladylike element somewhere in the outfit, though I felt okay in this one.
AM, yes, I'd wear the blue chinos with this moto jacket. The moto is actually a muted olive rather than black, but still, it would go nicely with the blue. I agree, I liked the outfit better with the moto on, though I ended up taking it off indoors.