chincac, I was very careful the first year I got them, then became less so the longer I had them. I have two pairs in box calf and the leather seemed a little different in each. The mocha pair (in Jumping boot style) has thicker leather and seems more hardy. The black pair (in Bardigiano style -- the same thing but with plain buckle instead of Kelly lock) has thinner, softer leather even though they are both Box calf. I had them both stretched about 1/2 inch so that I could tuck in my jeans. Before that I only wore them with leggings and tights.
The mocha pair is still stiff, the black pair less so. I don't think they stretched that much, but it could be because i already had them stretched. I wouldn't mind if the mocha would stretch a bit more.
They both still look pretty new to me, with some barely noticeable scuffs at the back of the heel (where the bootjack touches it when I use it to remove the boot) and a tiny bit at the front. The black shows less but I think I wore them a bit less.
I don't wear them if it's raining or if I think it is going to rain that day. But I have been caught in light rain and have had to step in a small pile of snow a couple of times when it was unavoidable (just yesterday in fact). They held up very well.
I once saw a woman at the Madison Ave store wearing a very old pair of Jumping boots with her jeans tucked in. The color was lighter than mocha, kind of like a British tan. She told me she wore them every year in every kind of weather. Hers definitely showed wear and tear, but they looked wonderful. Seeing her boots made me feel OK to wear mine without worrying so much.