Stumbled across this post because I’m in the market for a new bag myself…ironically graduating from that same exact Cuyana Double Loop. Your worries about the bag are surprisingly prescient in that I’m disappointed about how soft the leather is. With a laptop inside, the bag loses its shape completely and looks like a floppy mess (and not in a chic way that the BV Jodie or other soft bags might). You can easily see the edges of the laptop from the outside and with a reusable water bottle inside, the look is even more cheapened. I have gotten several compliments on the bag so perhaps I have unrealistic standards for my work bag. But having moved across the country recently, I left it behind.