Women's Classic Duck Boots: $69.50 at Lands' End
I know that tons of people swear by their Hunter wellies on rainy days, and I've spent much time this past year trying to decide whether or not to splurge and get myself a pair, but I've never been able to actually follow through and drop $100+ dollars on a pair of their rubber boots. Months into this never-ending debate, I randomly came across a pretty phenomenal discount on these duck boots from Lands' End through Lucky Magazine -- we're talking 50% off and free shipping -- so I took a chance, and I now consider them to be one of the best purchases that I've made this winter. I used to be the kind of person that was never prepared for messy weather and would often let a few rain drops totally sour my mood, but I actually like wearing these boots enough that I temporarily forget about the fact that the rain is ruining any chance I might have at a good hair day.
Disclaimer: If you decide to purchase a pair of these duck boots (or anything else) from Lands' End, please please please, do not do it without searching for a promo code first.