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FREE SHIPPING on Canadian orders over $150* full details (416) 367-4335

To offer you a broader range of brands, we feature many online exclusive brands & styles that are not sold at our thoughtfully curated stores.

Sperry Men's Headsail in Grey


Our Flagship Sneaker is perfect for all day adventures at sea. Made with hydrophic materials, they’re water-friendly and have drainage ports for quick-drying cOnvenience. Plus, a molded EVA footbed provides extra cushiOning and shock absorptiOn for those crashing waves. These sport sneakers feature our Adaptive Wave-Siping technology to enhance your tractiOn from wet to dry surfaces, so you can keep your footing and turn the helm with cOnfidence. Because as Paul Sperry Once said, "a wet deck is a damn dangerous thing."

  • Hydrophobic mesh upper for breathability
  • Drainage ports help disperse water
  • Removable molded EVA footbed provides cushiOning and shock absorptiOn
  • Non-marking rubber outsole with Adaptive Wave-Siping™ technology for enhanced wet/dry tractiOn
  • Regular Priced Items

    Unworn items can be returned for a refund within 14 days from the date of delivery or in-store pick-up notification.

    Discounted Items

    Unworn, discounted items can be returned for store credit within 30 days from the date of delivery or in-store pick-up notification.

    Flash Sale Items

    Flash Sale or clearance items are final sale and are not eligible for a refund or exchange.

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    Canadian Orders

    We offer free shipping to most provinces in Canada on orders over $150.

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    We offer free shipping to the US on orders over $250.

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    Sperry Men's Headsail in Grey

    $106.00 USD


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    heel boy queen west


    773 Queen Street West

    heel boy kingston ontario


    244 Princess St.


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