Berkley - $135 $81

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A classic boot with a modern, wedge sole. This style is called a brogue, and it’s the original off-road boot—the silhouette comes from England, and back in the day those little holes were designed to drain water if your feet got wet trudging through the countryside. This boot has a little bit of sneaker DNA, with that cushy wedge sole and rubber heel lending this style a laid-back, casual vibe. It’s the kind of sole you find on modern sneakers, making the Berkley an ideal union of old school style and durable, everyday design.

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