I love my leather ankle boots, so I'm super careful with them. I don't want to get them wet. And I did get them waterproofed when I first bought them.
But, I find that it can wear off after a while. I'm not sure if it's that I use my boots too often, or what.
But, anyway, I try to re-waterproof them every six months or so, particularly right before winter.
And they've lasted me a while. I've had to resole them twice already, but they still look great.