Get the Perfect Fit Those with smaller ankles should opt for a style that's tapered near the foot to avoid that too-loose feeling. If you have wider calves, pick boots with an adjustable top (try ones with elastic trim or lacing).
Find the Right Proportion The rule of thumb is the shorter the hemline, the taller the boot. Wear riding and similar versions with above-the-knee dresses or over skinny pants. Ankle heights work best with calf-grazing skirts (your tall boots will work with these as well).
Rubber with leather and metal chain, Love Moschino, $195; moschino.com.
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