I have a clear feeling that they (the founder Gary) do not make a new product unless they think they have a new slant on it, something which gives it a natural place in the world.
On top of that they put unusual amounts of thought and aesthetics into every product, and make them in solid quality. I have several of their products (from a wallet, over their smallest bag, up to their largest), and I would be surprised if any of them lasts less than at least a decade or two.
I just bought two new ones, their new backpack, Staad, and duffel bag, Outback. I'm looking forward to getting them next week.
If you feel like treating yourself, I recommend them. (And and the smaller products won't break the bank.) Say hi from Eolake, they know me.
(I'm getting the left one, dark leather accents on 'ballistic nylon' which is really light and strong.) (I've petitioned them to find other colors than black for the "ballistic" as they call it, as a gadget fan, almost everything I own is black, it gets a little monotonous.)
Update 17 June: Today I got the Outback.
It will replace my old travel bag, which I bought a decade ago in a chinese shop for less than the price of a pack of cigarettes! As a matter of fact, it's not that badly made, and was certainly high value for money. But there's just no comparison. The aesthetics and the quality of the Waterfield makes it an ongoing pleasure to use, instead of a merely-functional item. It's stronger too, and the flexible division makes it highly useful.
I took photos of them together. Sadly they can't show the feel, but maybe they can show some of the quality difference. The leather, the metal connectors, etc.
Update II: win a Waterfield in our photo contest.
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Below is one I admire, the Rough Rider, but probably won't get because I have enough messenger bags and brown leather is not for me (the black is, and it has a great feel. But very few products of theirs are made in that). But it shows their design aesthetic to the fullest. (Though it's perhaps the only one of their bags to not have their nice "golden" lining which puts light inside the bag when you need to find something.)