It needs to be leather, in a tan or lighter brown shade. It doesn't need to fit a laptop. Messenger style bags are too narrow, and I don't like satchel style either. I always carry a paperback and a water-bottle. I want it to have a shoulder strap but I like grab handles too. I like a softer, unstructured sort of look rather than anything too boxy. I don't mind if it has pockets or not.
I like Fossil, but the Rachel Satchel seems a bit small. The Fossil Maya satchel is a contender, but I worry it is a bit frumpy looking?
Budget is 250.