I don't own either bag but I absolutely love the way the 16 bag looks. It's rare for a bag to be love-at-first-sight for me, but this one definitely did that for me.
I think that the grained calfskin version would be more practical, even though you said you like smooth leather more. While the satinated calfskin feels a lot more resilient than box calfskin, a grained finish can hide scratches, and also water damage should your bag get caught in a downpour. Smooth leather would show the resulting damage more.
The Luggage has an open top, so it will be easier to get things in and out of your bag, much like your Sac de Jour. But the 16 looks a lot more elegant in my opinion.
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