What would Clinton and Stacy do?

I've been hearing the call for some time now. It had grown to "deafening." The daily visual reminders were too much.

I had to clean out my closet. No longer could I avoid the entangled mess of wire and plastic and rumpled, dusty clothing. The time had come to purge, purge, purge.

It doesn't matter how many times a year I do this, I seem to end up with the same amount (2 large plastic bins full!) of clothing to give away. I can't make it make sense, as I so rarely buy clothes for myself. Especially the kind that hangs in the closet. The only explanation is that they multiply after midnight.

So this morning I started digging. Digging and digging and digging. Clinton and Stacy would be proud. Out went the last remaining sweater set, the ankle-length denim skirts, the dress I wore to my cousin's wedding ... 10 years ago.

Here is where I always have trouble. Say there's a dress (or suit or shirt) in excellent condition, still sort of "classically stylish" hanging faithfully in your closet. With a little work, you can remember the specific occasion for which it was purchased. A little carbon dating and you can place yourself in that piece of clothing for the first time somewhere between 8 and 10 years ago.

What do you do? It's a perfectly good item, except for the photos of you wearing it almost a decade ago. Do you count it as a good investment, thank it for its years of service and reassign it to another post, simply because it's old? Or do you wear it proudly, displaying your ability to select pieces that just simply don't go out of style? Or do you invite a friend over to tell you whether or not you should be caught dead in it anyway?