The first ugly shoe I remember desperately wanting was the Earth shoe. It was so ugly it was cute. Plus the "negative heel" was designed after the shape of a bare footprint in the sand, so cool! My parents couldn't afford them, so I got a knockoff pair at Thom McAn. The shoes were suede instead of smooth leather, and the color was chestnut instead of walnut, so I was glad when the upper split from the sole and I could retire them.

The second ugly shoe I loved came just a year or two later, in college. A friend of a friend let me try on her Birkenstocks, and I was completely in love, a feeling that has never entirely left me. (Besides, I hear Isabel Marant was recently spotted at the farmer's market sporting a pair of Birkenstock Arizonas.)

On to many others that I've loved. I've developed a theory that there is always at least one "Ugly Shoe of the Moment." With this shoe you can be both fashionable and comfortable. Usually the shoe is not flattering (that's why we're calling it ugly). But it's *in*, and your feet are in heaven!

I've been all over this idea since I first loved the Earth shoe. I've discovered that it's very important to choose the "in" variety of the shoe--you need to be careful with lesser worn styles and colors, because then you'll lose the It factor. If everyone is wearing white Reeboks and you get gray, you'll feel silly even if you made the determination that gray worked better with your wardrobe. And careful about getting low Docs if the look is high tops.

I had an epiphany of sorts maybe ten years ago in a rainy college town that shall remain nameless. I noticed that all the women my age were wearing name-brand Gore-Tex parkas, along with seriously expensive practical shoes. Just the style I aspired to. And I had an uncharacteristic thought, for me--that for the amount of money they were spending on their clothes, they could look GOOD!

But--in my down time--I still love me an ugly shoe of the moment. Do you?