Thanks
odd.
I'll post pics soon. I know what you mean about the City being kinda boxy but its silhouette is similar to that of Hermes Birkin or Kelly which are (IMO) the epitome of dressy. I don't have a Twiggy but I did try one on and it felt more casual. I agree with
KristyDarling that its duffel shape gives it a sportier look. Did you put on a dressier outfit and and try them both on to see the full effect? I was thinking the City will echo the lines of your gaucho pants and a-line skirts. Besides, as most b-bags owners can attest, you'll probably end up getting the other style at some point.