I think the hobo is quite sharp looking but I don't own one.
The Day is by far my favorite style. It works on tall and short, petite and big boned. It is an effortless looking bag--relxed but luxe. It's quite practical. I use the outside pocket for my phone and keys. It is a deep bag and sometimes I do dig around a bit for my wallet. But perhaps that extra two seconds have saved me from a silly purchase or two!