Go for it - I do it all the time. I've got 4 large n/s hamiltons, 3 chain ID hobos, 2 Gansevoorts, and 2 Uptown Astor large shoulder totes.
I haven't seen the Gansevoort in python irl, but I bet it's totally gorgeous!!!
Oh girl! You should do a collection shot, I would LOVE to see your MKs!!