Best Bet: Reboot Your Raingear
Kenneth Cole's waterproof motorcycle boots are both practical and trendy.
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Best Bet: Get the Boot
These chic, wearable fall boots are part of Pierre Hardy's latest collaboration with the Gap.
Best Bet: Re-Boot
These wool-and-rubber boots are durable, but don’t scream “galoshes” like the chunky, upturned toe of Hunters.
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