Ever since I can remember, I’ve been on a quest for the ultimate handbag. I’ve had bags that were like luggage:

How could you not love this?

Bags that were actually boxes with handles:

Frankly, a good box purse is still my first choice

And bags that had pockets for everything:

Okay, this one's really more of a backpack.

But each one left something to be desired. What am I looking for? Something that goes with everything (so, black or brown leather would be ideal), but that has more pockets than just a simple bag. Something that is spacious enough for my tendency to over-prepare (I generally have at least two small notebooks, four pens, seventeen lipsticks, a phone, a large wallet, another wallet with all those stupid loyalty cards, a brush, an iPod, earbuds, and forty-seven receipts, and that’s when I travel light). Something that looks nice, but not too pretentious.

This, for example, is a little too pretentious for me. Just a little. A smidgen.

The fastening has to be secure, but easy to open (don’t say it, I know that’s an oxymoron). And it has to have a shoulder strap. I am normally juggling five things in my hands, and I don’t want my purse to be one of them. At least, not until I have staff that follow me around, interacting with the world for me so that all I have to do is hold my tiny yappy dog and tea.

I think I may end up getting…

wait for it…

a diaper bag.

Think about it. Diaper bags are the epitome of “holds a lot of stuff.” And modern designs are pretty posh looking! But I’m trying to decide whether giving in and buying a diaper bag as my regular carrying-around bag is the clutter equivalent of giving up and wearing sweats all the time. Clearly, I’m going to have to angst over this for a while longer. And keep switching my stuff between the three purses I have now that I hate and love in equal measure for all sorts of different reasons.