I got a velo as my first bbag because I'm into cross body bags, I'm 5'3 and it does ride a little bit low... (I'd say right below the hip bone). But it doesn't bother me as much, plus I love the extra height (it has a squarish shape while the city has a more rectangular shape).
But if you're not comfortable wearing your bag real low and don't need the extra height. Then I'd say go for the city. So it really depends on your taste and criteria.
I am seemingly tall (5'7/8) and it bothers me when messenger bags lay on my thighs/butt. Even small bags. The City isn't comfy to wear cross-body (though possible), but I think it is the perfect length. It lays comfortable of the midsection.