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The Authentic Original™ Double Sole Chukka offers a bold new take on a coastal classic. Our iconic Authentic Original™ boat shoe upper has been reimagined as a mid-cut chukka, crafted from premium leather, with traditional moccasin construction. The preppy upper sits atop a double sole, which is finished with our signature razor-cut Wave-Siping™ technology for superior traction. Pair these chukkas with your favorite jeans for a standout look this fall and winter.

Sperry Authentic Original Chukka Boot In Brown
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First seen in Aug 2025
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SPERRY
Authentic Original Chukka Boot In Brown

$140
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Sperry Authentic Original Chukka Boot In Brown
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Product Details
Sperry Authentic Original Chukka Boot In Brown

Authentic Original Chukka Boot In Brown

The Authentic Original™ Double Sole Chukka offers a bold new take on a coastal classic. Our iconic Authentic Original™ boat shoe upper has been reimagined as a mid-cut chukka, crafted from premium leather, with traditional moccasin construction. The preppy upper sits atop a double sole, which is finished with our signature razor-cut Wave-Siping™ technology for superior traction. Pair these chukkas with your favorite jeans for a standout look this fall and winter.

about SPERRY
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Paul Sperry was an avid sailor who almost lost his life to a slippery boat deck. Turning his eye to innovation, he spent years experimenting with non-slip shoes. Upon witnessing his canine friend move effortlessly across ice, the talented craftsman decided to mimic dog paws on the bottom of a rubber sole 'thus the world's first boat shoe was born in 1935. Today, Sperry Top-Sider has grown into a full line of covetable swimwear and accessories. Men's Sperry Top-Sider shoes are imbued with a preppy, East Coast appeal. Featuring trademark grooved soles, each slip-resistant deck shoe, boat shoe, boot and sneaker is the perfect holiday companion. Choose from comfortable leather, suede and canvas designs to suit a wide range of occasions.
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