i used to own the bordeaux shrug from last season, then my car got broken into and it was STOLEN.
BUT, I do own a choco brown hobo too. so i can definitely compare.
if you want an everyday bag, they are both great. it depends how much you want to hold and What you want to hold.
the shrug is good for essentials. it's easy for you to get into b/c there's no zip, just a flap (not theives, don't worry, b/c of the way it sits under your arm). the flap though keep in mind, won't button if you're carrying files or paperwork b/c it won't reach over.
BUT if you need it to hold things like a light sweater, shoes, files, the day/hobo is a GREAT size. i LOVE the hobo (the darker colors lend a more professional/formal look). anytime i need to go somewhere after work and don't get home to change & get ready, the hobo is great. it never gets too heavy carrying all that stuff either.
it's very deep though, so when i used it for just essentials, that got to be annoying to search in the depths of the bag. so i used to switch between the shrug and hobo.
hope this helps!
. But I don't know if the First is the right size for me 
