Hi!
I was in such a huge dilemma before I bought my first Bbag 2 weeks ago. Pictures are DEFINITELY deceiving. Bbags look way bigger in pictures than in real life. I originally thought the City was HUGE from looking at mod pics here on tPF, that's why I was considering the Town. However, when I actually tried the different styles on in store, my mind was blown. The City is the perfect size. The Town is actually smaller than I thought and the First is extremely tiny.
With that said, I purchased a black City in mini rosegold hardware and I absolutely love it! I can fit a wallet, keys, phone, water bottle, small makeup bag, tissue, and other small essentials. Hope this helps!