So, it turns out that I am NOT allergic to my wool socks. I must have stepped in some poison ivy (or something similar). Each week I wore the boots, I would get an itchy rash on my ankles. The last time I wore the boots, the rash was the worst and lasted for over two weeks!
I bought new boots after reading that the oils from the poison ivy can remain in the boots for up to a year. I'll start breaking them in next weekend over the Labor Day weekend.
Chris came home from his work trip with similar itchy feet. I can't imagine he got it from my boots, but perhaps something he encountered in Park City during his meetings last week.