Agree with @earswithfeet - the fortune cookie shape when using the strap and with @ghoulish about banging into everything when hand held. I do use other handle bags but I can't recall any of them bumping into things more than the City.I'm curious, to our friends here who are not fans of the City, what about them doesn't work for you? @muchstuff?
I remember when I first started collecting, I preferred Days and Works because I could fit my laptop in them. I loved the-more-leather-the-better Work, but didn't love the hand or arm carrying. Over the years, laptops became more and more compact and could fit in the City. The City has taken over the Work for me because of this detail and the preferred shoulder strap.
The Day is my favorite style and the most comfy for me