Cobalt Blue Suede TOMS (the half of my genes which hail from Memphis are going "hell, YES" to these)
Maestra Botas: these are the newest flavor of TOMS, and they're all-weather. I didn't like them at first, but seeing what they look like on folks has changed my mind. They also have them in this kind of awesome plaid print, but those are fleece-lined, which is way too much insulation for my tootsies.
Most importantly, of course, is that purchasing any pair of these means you've also purchased a pair for a child in need.