As you can see from the avatar, I have all three. The cocker, woven hobo and ball bag. Out of all three, I like the cocker the best for everyday use. I can be used to dress up or down. It's so comfortable and I admire the luxurious thick supple calf leather on the non-woven portion. The leather seems like it's very durable too. I love how it slouches and the feeling of holding onto the braided handle. It's more comfortable to get in and out of b/c of the magnetic flap top. It fits just as much as the other three b/c of its width, and just love the 2 extra pockets on the side for easy cell phone, compact access. I would get the dark chocolate color as it looks very rich and luxurious. I saw a lady carry one and it looked so nice. Black is nice too, but you can't really appreciate and leather and the details of the bag on a black color as much as the brown.
The drop on the bag once you have things in it is more than you'd think. I can comfortably wear it over my shoulders, and just tuck it back a bit. It fits fine w/a wool coat on. HTH!
If I had to do it all over again, I would get the cocker 1st, then the hobo, then the ball bag.