I sold my city a long time ago too. I believe I felt it was too small but now I carry even smaller bags so it could work. But there might have been an additional reason I sold it that I can't remember. I think it didn't wow me. The stewardess has a more comfortable strap but I think it is rather short. I sold that one too. I think I didn't like the chunky look. I prefer the streamlined look of the Ranch bag but it doesn't have as comfortable of a strap.
Yea, the city bag is very “plain” for lack of a better word (not a bad thing). If I come across one for a good price, I think it’s worth a try again. Maybe you should try it again as well? I bet you can find them cheaper on US Poshmark compared to Ebay
The city is definitely nothing fancy. I guess it's just a good size for me. I like small bags, but it's a little bigger for when I need to carry more.