I've owned both, and after using both for a long time, I can honestly say that I prefer the Day. Don't fear it being too big; it's only a little bigger than the City, it's just that the space is distributed differently. The City is great and a classic Bal - but ultimately I find it to be a little too fussy for me. I LOVE the look of it, but the double-zippers make it a little harder to get in and out of the bag. And there are too many things hanging off it - handles, strap, floppy ears. Great for looks, but a bit too much for me in terms of function.
The Day offers deeper pockets (and yes, they're enough to keep me organized; for the rest of the little stuff that can get lost, I use a Makeup) and one single handle that stays on - and I don't worry about it getting dark the way I worry about City handles. GH Days are lighter than GH Cities - so if you're considering getting one with GH, that's a factor.
They're both great bags, and they both look fantastic when broken in. And I agree with everyone, the Day seems much smaller once it's been used a bit. Still fits a lot when you need it to, but slouches nicely when you only carry a few things.
The Day offers deeper pockets (and yes, they're enough to keep me organized; for the rest of the little stuff that can get lost, I use a Makeup) and one single handle that stays on - and I don't worry about it getting dark the way I worry about City handles. GH Days are lighter than GH Cities - so if you're considering getting one with GH, that's a factor.
They're both great bags, and they both look fantastic when broken in. And I agree with everyone, the Day seems much smaller once it's been used a bit. Still fits a lot when you need it to, but slouches nicely when you only carry a few things.