Vera Bradley's "Vera" tote... Lots of inside pockets and just the right size overall. Certain patterns are almost always on sale (although it's still a bit pricey).
Marc Jacobs Eliza bag. It is gloriously large, has a million pockets, and is made out of nylon so it is lightweight and easy to wash. It looks brand new and dd is ten months old. I was stalking mine online and finally found it on clearance at saks. You could find it less expensive on like eBay or on clearance at Nordstrom or something... I think the prints are updated yearly...
Re: Diaper bag
I really like my Petunia Picklebottom.
It's expensive but it's 2 years old, looks brand new. I'll be using it again.
Also has tons of pockets for the little stuff and center compartment is big enough for cloth diapers no problem.