The classic LL Bean Duck Boot is considered an acquired taste by some. For a picky UrbanPrepstress-in-training, may we suggest the Polo Ralph Lauren Pony Print Rain Boots ($40). The seamless construction and breathable cotton liner will keep her feet warm and dry, which is important as she is sure to ignore your pleas to stay out of puddles with the same joie de vivre she will someday display for skirting the dress code at Choate.