Here is a picture of my bag now, after almost two months of use.
Bathroom has the best lighting!
The little pouch that comes with the tote is completely useless. The size seems decent, but it is sewn so tightly that you can't get much in it. My phone doesn't fit in it, and I would be reluctant to stick credit cards or my drivers license in there. So nothing is in it, but I still leave it attached to the bag. Mostly from laziness. Perhaps I will stick a lipbalm in it.
The fact that the bag is one big pouch is slightly problematic if you are not organized. It becomes a catchall for everything. And with only one compartment, when the phone rings it becomes chaos to wade through the crap to find it. I have resorted to buying little zipper purses for it. One for my travel essential oils, one for first aid stuff, you get the idea. It's not such a bad thing because when I want to switch purses it's easier in that way.
Cost ended up being the largest factor on why I purchased the JCrew vs. the Madewell. I ended up paying $117 after taxes for the Downing Tote, and the Madewell Transport is $168 before taxes. I think the zigzag adds something extra to the JCrew tote, but in hindsight, I probably would try and save up longer to purchase the Madewell bag. I think that small zipper compartment on the Madewell would be well worth it.
For what it's worth though, I do have the Madewell Kensington Satchel, and even with all the issues with the J.Crew bag, I prefer it to the satchel. Mostly because the JCrew tote is larger, and I am the type of person who likes a bag to be big for books. And with 5 kids, my lifestyle isn't so much zippered up purses. I need to be able to access the contents of my purse quickly!