I have a pair of ankle-high Cabela's leather hiking boots that have been to Hell and back. They look rough but they're super comfortable and tough. I'm probably another year or so away from having them resoled or replaced.

To replace those, I bought some taller (higher up on the ankle) Rockports. I wore these just enough to break them in. My plan was to put the Cabela's in the car and have the Rockports be my main pair of boots, but I changed my mind and put the Rockports in my car kit. They're too pretty for rough use .

The newest pair are Merrel's, ankle-high light-hikers. Sinfully comfortable, feather-light and great looking, I wear these on snowy days going to customers and the office.

All three are waterproof. I don't buy boots that aren't.