A rain boot that attempts to mimic a regular boot too closely will never succeed. It will always just look like a really clunky rubber shoe. And I'm not sure I can get behind a rain boot with a significant heel. But one thing I can resist no longer are the adorable ones high-end designers are turning out. From Dior and Chloe, to my personal obsession, Tory Burch, which have an old-timey equestrian feel, I've been coming across a whole new crop of these, seemingly paradoxical, wonderfully indulgent necessities. See: The September InStyle which has a whole page devoted to the new set in the Shop It! section (Pg. 388).
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