I'm a bit tired of looking at sandals so for some relief I thought it would be fun to play a game. Imagine:

You just won the lottery so money is no object. I'm going to introduce you to the magic cobbler. He's amazing! You bring him your shoes, he looks at your feet and he gives you a foot massage. A few days later you return to his shop to pick up your shoes and find that he has transformed your shoes-- by feel only-- into the most comfortable, walkable 24-hour shoes you have ever owned. They will never get dirty and no matter how you feel about your feet, ankles and legs, when you wear these sandals these parts of your body look stellar. So which pair of killer sandals did you run out to buy? There are no constraints, except one. Since you have plenty of money and are now buddies with the magic cobbler, you can buy a killer pair of sandals every year. So the sandals you choose today have to be available in 2009.

P.S. Don't feel obligated to go searching for the perfect sandal. If you feel you have a killer pair of sandals in your closet already, that works too.