I'm looking for something that I can wear out in the rain, either to work (I work at a Startup) or out at night. Basically a dressy, waterproof sneaker or low-cut boot.
Danner Men's Jag Wool Ankle Boot
Russell Wilks
19 Karma
If you're willing to go with a low-cut boot, these are another good option. I tried them for a while and they're solid, but they're heavier than a sneaker (though not as heavy as most boots).