I went through the same thing when I was figuring out which to buy as my first bag. I went with a city b/c I figured I wanted the "classic" bbag style. I did get a twiggy as my second though and I would say style-wise, I love them equally! Yeah, I'm not help - go with what you think will work for you more functionally. I do think my twiggy lays better when on my arm/strap than the city, if that helps at all.