I am an educator and mother of three. Our family's adventures have moved us from Utah to Boston to Paris to New York City. We are currently living in Arizona, where the excessive heat is an adventure unto itself.
If Santa happens to be bringing your littles rain boots this Christmas, you should probably have a look at the current offerings from Mini Boden. Their kids' Wellies (girls' here and boys' here) are about the cheeriest I have ever seen. So cheery, in fact, that convincing kids to wear socks with their boots may not even be much of an ordeal (am I the only one whose children will not wear socks with their rain boots?). These boots, and many other cold-weather staples, are on sale right now at Mini Boden for $23.40 with free shipping. That's 35% off which is perhaps not too bad considering that Christmas has not yet come and gone. I think that they only danger in buying these is that your kids will never want to wear any other footwear again.
To dress a child thoughtfully needs not be prohibitively expensive. Here you will find resources for buying beautiful, well-designed clothing at surprisingly low costs. Diminutive clothes, diminutive style, diminutive prices.