The goat leather on these bags are very thin and delicately soft (but they are pretty sturdy), so the City won't be able to hold itself up since it's not a structured bag. If you just let the bag sits there w/o anything in it, the bag will collapse. That's why most people have a hard time photographing these bags w/o stuffing it. If you have things inside the bag, the bag will sit up more. KWIM?
If you have the really smooshy, yummy old leather it won't sit up empty. I have all 05's because it is my favorite leather. I will confess a secret here, I stuff my bags with old clean white t-shirts and one fresh dryer sheet to store them or put them to bed (which everyday they go to bed no matter how long it takes to empty my stuff), and then when I take them out to go, if I don't need to bring alot of things with me I leave some of the shirts in the bottom to retain the shape of my City's and my Box. Now the only exception is my new 05 Turq Twiggy. Since I don't like the long shape, I prefer how it looks more empty and slouchy, so she can go out without stuffing. So here is a picture of my bags completely stuffed!