As someone who made this decision back in fall, I’d pick Chanel 19. Although both are not the classic flap, 19 has more of the classic flap feel, therefore I thought it would have more staying power. I also think the style - shape of 19 is more versatile Can be dressed up or down, and Gabby has more of cool/casual everyday look. So boils down to what you are going to use it, what else you have in your collection. I only had a small boy and wanted something that I can fit more, can be used for variety of outfits and occasions.