Meet the beautiful How Does She Do It by Stella and Dot.
I took this bag to work, to the gym, on errands, to the park, to happy hour, anywhere and everywhere. It's light enough to carry on a two mile walk, functional enough to survive a 15-hour day-to-night extravaganza, and beautiful enough to incur compliments from strangers.
Best feature: the How Does She Do It transforms from a carryall to a satchel with two side snaps. The sides fold in to create a rounded top, as pictured above. I tended to carry the bag on my elbow in satchel form and over my shoulder as a carry all.
My bag was a little stiff, which made it hard to transfer from the carry-all to the satchel form. But with about two more days of wear that stiffness would have worn off. The canvas is pliable and lightweight, somehow without sacrificing a beautiful texture and feel. And, although I didn't test this, there's a "spill resistant" coating that makes me feel great about choosing the navy and white striped option.
The orange polka dot lining is divine (you can see it peeking out here). There are several inner pockets including a nice large zipper pocket. And, best of all, a little side inner pocket specially made for a water bottle. A single open side pocket (also lined, beautiful!) is perfect for go-to items, I mostly used it for lip gloss, my phone and earbuds. The whole thing zips up on top, making this a great buy for the airport or busy city streets. 
On the website, Stella and Dot describes this bag as "...a carryall (and boy, do we mean all)." They really do. I put this bag through the ringer. I carried a set of Halloween lights, lint roller, heels, a bottle of wine... really I threw in anything I could find. It carried it all. So often lightweight bags feel flimsy, but not this one. I trusted this bag completely, enough to carry a 13" Macbook. It handled it beautifully with room to spare.
Final decision: If you're an on-the-go kinda lady, make this investment. At $89 the How Does She Do It is a steal. You'll thank me later.
Many thanks to the lovely Erin Markland, an incredible stylist and Stella and Dot's youngest Director, who introduced me to this beauty. If you're ready to transform your style, she's the one to call.