Best Bet: Re-Boot

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Photo: Courtesy of J.Crew

Fall weather in New York is frustratingly unpredictable, and if this summer is any indication, we’re in for a dreary season. We’ve been on the hunt for the perfect set of rain boots for years — pairs we’ve previously beaten into submission either feel like bricks strapped to our feet or make us look like we’re 6 years old, splashed with candy-colored patterns and trim. These waterproof wool-and-rubber boots are durable, but don’t scream “galoshes” like the chunky, upturned toe of Hunters. And their matte finish is more understated than the typical glossy, reflective sheen, so you can shamelessly wear them out even in clear skies.

Wool-and-rubber riding boots, $120 at J.Crew or online.