Hi! I was just in the Tory Burch boutique today and tried out both of these bags. The SA let me fill each bag with my stuff so I could get a good feel for them. The city satchel is softer and smooshes down quite a bit but the handles don't come down around the bag when you attach the shoulder strap. It also does not have metal feet to protect the bottom. The leather is lovely tho and it's a beautiful bag. The Robinson is a stiffer leather but does give a little bit and so it does not appear to be a frame type bag when filled. It has metal feet and side patch pockets that are nice for storing a phone and little items for easy reach. The Robinson is a more classic looking bag while the City looks more contmporary IMHO. In the end I got the Robinson because I think it will fit any occasion. Hope this helps.Does anyone have the Tory Burch City Satchel? I cant choose between the Robinson Satchel and the City Satchel, I like the way the City Satchel leather looks softer.