Reissue in 227 size. I personally, really don't like the jumbo size, esp the ones w/ the new chains. the reissue is the same length and height but the width is smaller, it's flatter than a jumbo. The drop of the reissue is also shorter than a jumbo. The jumbo just looks like a messenger bag with chains. It ALSO depends on your frame. You will not be dissappointed. It's chics up any outfit.
For durability, though the jumbo wins because it is caviar. But the reissue leathers look much more luxe than caviar. I do own caviar but in the medium size and it's very lovely with gold hardware.