Right now I've got a pair of Columbia Hiking boots, 8'' ankles, water proof (dunked my feet in the bath tub, and socks came out dry), and rated to keep my feet warm in weather down to -32 degrees. Fucking great boots... wear 'em for work too.
The only downside (and this goes for every pair of footwear, boots/shoes, whatever)... I broke the laces the other day, so now I have to tie my right boot twice... once where the foot meets ankle, the other at the top of the ankle to keep the support.
Still though, comfy effing boots.
$100-120ish at National Sports.
"War must be, while we defend our lives against a destroyer who would devour all; but I do not love the bright sword for its sharpness, nor the arrow for its swiftness, nor the warrior for his glory. I love only that which they defend: the city of the Men of Numenor, and I would have her loved for her memory, her ancientry, her beauty, and her present wisdom. Not feared, save as men may fear the dignity of a man, old and wise." - J.R.R. Tolkien