SO I started a new search - one for a diaper bag that didn't make me feel like I was starting down the path that ends with 'Mom Jeans'. It was harder than I thought. There are a lot of cutesy fabric bags out there, overly utilitarian bags, and just plain ugly ones. I am not sure when in the process I decided to abandon the search for a diaper bag and find a regular tote that will carry diapers and what not.
I found several great over sized handbags by designers like Chanel and Gucci that I was able to justify being a diaper bag. Problem was that the hubby did not agree with my justification and I was told several times in Neimans to "keep walking".
As it turns out, conducting my search as the summer season was approaching was very beneficial- if it will work as a beach bag the transformation to a diaper bag is pretty easy. Stores, magazines and designers are all too eager to present us with multiple 'style guides' for what you need each season and during the summer we all need a beach bag. That is how I decided on diaper bag #1.
I originally was headed to buy this Tory Burch tote in one of the Spring/Summer '12 colors but opted for the all black since it will be better year round.
Diaper Bag #2 came about while looking for something that Jason would at least take with him, ie: leave in the truck. This is what we (OK, I) decided on. Jason doesn't hate it, I really like it and it is virtually indestructible. I still have my set of Jon Hart luggage from high school graduation (including a makeup bag I use almost everyday) and it is all still in great condition. Seriously after a nuclear bomb goes off we will be left with cockroaches and Jon Hart luggage!
Along the search I found a few other acceptable bags like these from Rosie Pope (left) and Timi & Leslie (right). Plus they are both still affordable.

And of course the Rebecca Minkoff 'Knocked Up' bag. Not so much affordable- but fabulous.
With the bags at home and waiting for baby now all I need to do is fill them! So moms out there, what items did you find to be the most helpful in your diaper bag?