There are many things that must be considered when approving said bag, and there is a long checklist of qualities that must be present:
1. Must have long handles, to allow me to fling it over my shoulder, but not be so long that it hits the ground when I hold it to my side.
2. Must have several interior pockets and dividers.
3. Must have a special place for cell phone.
4. Must be cute. Birds optional, but desired.
5. Must accommodate an umbrella and a water bottle.
Now, one would think that this would be an easy task. An easy find. Alas.
There have been many that seem to fit the bill, but I have yet to find perfection.
The bag on the left is my current go-to, but it's too bulky. The bag on the right is adorable, but has no compartments and isn't wide enough to fit a folder.
Additionally, I carry so much crap around with me that it's just stupid. I blame this on my years living in DC, where I took tons of stuff with me when I left the house each morning because I rarely knew how soon I would return. That's also where the umbrella requirement comes from - when I walked everywhere and took public transportation, being stuck without an umbrella was pretty much the worst thing that could happen.
Things I carry around on a daily basis:
keys, wallet, phone, chapstick
tea bags, gum, snacks, candy, almonds
pens, umbrella, personal care pouch-y thing
planner, book, water bottle, coffee cup sleeves
This doesn't look like much, but there are a good number of things missing, including the umbrella. Way too many things, really. So having a bunch of compartments is important to me - having to deal with a tote bag with its undisciplined cacophony of things would drive me to drink.
And I really wish that this thing didn't intrigue me, because it is so ugly and tacky, but it does: