+1
Which one would you reach for more. Personally I find carrying a shoulder bag more comfortable and easy to carry so I would choose to keep the Caissa Hobo.
I love hobo bags (not all, of course) and I do have a secret crush on Caissa Hobo (as I do understand it has feet as well, if yes, wow hobo+feet). Either way, they both look great.
Kensington. Its more classy. But the hobo bag i think is lighter. I dont have the caisa hobo so i cant compare, but i just bought a kensington and its not heavy for me.
The Caissa. It just looks more comfortable to wear, can be dressed up or down, and the external pop of red is quite eye-catching. The Kensington, for whatever reason, always strikes me as a cold, rigid, and impersonal design.
I love the cassia, but I also have an interest in the Kingston as well!! It's so hard. But I think I would choose the cassia. Good luck on your decision!!!