Phone
    Call
    1 (888) 200 - 8414
    Mon - Fri: 8:00 AM - Midnight ET
    Sat - Sun: 8:00 AM - 11:00 PM ET
    FREE shipping and FREE exchanges. every day. no minimum.
    0 Cart
    Loading...
    Your cart is currently unavailable
    Loading...
    Advanced search is currently unavailable

    Paul Sperry, founder of Sperry was an avid sailor with a passion for adventure. He was an inventor, a sailor and an intrepid explorer. An independent...

    Sperry Top-Sider

    Sperry Top-Sider Mens Boots

    1-25 of 25 results
    Sort by
    Display
    Sperry Top-Sider A/O Wedge Leather Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Leather Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Leather Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Leather Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider A/O Wedge Leather Chukka Boot(
Men's) -
Black Leather/Suede
    New
    Sperry Top-Sider A/O Wedge Leather Chukka Boot(
Men's) -
Navy Leather/Suede
    New
    Sperry Top-Sider A/O Wedge Leather Chukka Boot(
Men's) -
Sahara Leather/Suede
    New
    $119.95
    Sperry Top-Sider Fowl Weather Chukka Boot (Men's)
    Sperry Top-Sider Fowl Weather Chukka Boot (Men's)
    Sperry Top-Sider Fowl Weather Chukka Boot (Men's)
    Sperry Top-Sider Fowl Weather Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Fowl Weather Chukka Boot(
Men's) -
Black Waterproof Leather
    New
    Sperry Top-Sider Fowl Weather Chukka Boot(
Men's) -
Dark Brown Waterproof Leather
    New
    Sperry Top-Sider Fowl Weather Chukka Boot(
Men's) -
Navy Waterproof Leather
    New
    $89.95
    Sperry Top-Sider Dockyard Chukka Boot (Men's)
    Sperry Top-Sider Dockyard Chukka Boot (Men's)
    Sperry Top-Sider Dockyard Chukka Boot (Men's)
    Sperry Top-Sider Dockyard Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Dockyard Chukka Boot(
Men's) -
Burgundy Leather
    New
    Sperry Top-Sider Dockyard Chukka Boot(
Men's) -
Dark Brown Leather
    New
    Sperry Top-Sider Dockyard Chukka Boot(
Men's) -
Tan Leather
    New
    $149.95
    Sperry Top-Sider Decoy Duck Boot (Men's)
    Sperry Top-Sider Decoy Duck Boot (Men's)
    Sperry Top-Sider Decoy Duck Boot (Men's)
    Sperry Top-Sider Decoy Duck Boot (Men's)
    Sperry Top-Sider Decoy Duck Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Decoy Duck Boot(
Men's) -
Amaretto/Black Full Grain Leather
    New
    Sperry Top-Sider Decoy Duck Boot(
Men's) -
Dark Green Full Grain Leather
    New
    Sperry Top-Sider Decoy Duck Boot(
Men's) -
Dark Tan/Navy Full Grain Leather
    New
    Sperry Top-Sider Decoy Duck Boot(
Men's) -
Tan/Brown Full Grain Leather
    New
    $119.95
    Sperry Top-Sider Gamefish Mukka Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Mukka Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Mukka Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Mukka Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Gamefish Mukka Chukka Boot(
Men's) -
Avocado Textile/Synthetic
    New
    Sperry Top-Sider Gamefish Mukka Chukka Boot(
Men's) -
Navy Textile/Synthetic
    New
    Sperry Top-Sider Gamefish Mukka Chukka Boot(
Men's) -
Smoked Pearl Textile/Synthetic
    New
    $99.95
    Sperry Top-Sider Gamefish Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Chukka Boot (Men's)
    Sperry Top-Sider Gamefish Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Gamefish Chukka Boot(
Men's) -
Black Nubuck/Wool
    New
    Sperry Top-Sider Gamefish Chukka Boot(
Men's) -
Grey Nubuck/Wool
    New
    Sperry Top-Sider Gamefish Chukka Boot(
Men's) -
Taupe Nubuck/Wool
    New
    $109.95
    Sperry Top-Sider A/O Wedge Suede Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Suede Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Suede Chukka Boot (Men's)
    Sperry Top-Sider A/O Wedge Suede Chukka Boot (Men's)
    New!
    Sale
    Sperry Top-Sider A/O Wedge Suede Chukka Boot(
Men's) -
Dark Grey Leather/Suede
    New
    Sperry Top-Sider A/O Wedge Suede Chukka Boot(
Men's) -
Grey/White Leather/Suede
    New
    Sperry Top-Sider A/O Wedge Suede Chukka Boot(
Men's) -
Tan/Burgundy Leather/Suede
    New
    $119.95
    Related Products
    Add elegance to your look wearing the Stacy Adams Madison II Plain Toe Chukka Boot. Leather linings offer a luxury ...
    Stacy Adams Madison II Plain Toe Chukka Boot
    Description:
    Add elegance to your look wearing the Stacy Adams Madison II Plain Toe Chukka Boot. Leather linings offer a luxury feel while its genuine Goodyear welt construction lend dependable durability. Genuine Goodyear Welt ConstructionLeather LiningLeather sole Additional Info Goodyear Welt ...
    The Timberland Earthkeepers Britton Hill Chukka is an environmentally friendly twist on a classic favorite. The eco-friendly, Silver-rated-tannery-produced premium leather ...
    Timberland Earthkeepers Britton Hill Chukka Boot (Men's)
    Description:
    The Timberland Earthkeepers Britton Hill Chukka is an environmentally friendly twist on a classic favorite. The eco-friendly, Silver-rated-tannery-produced premium leather upper features perforations and contrast stitch detailing. Breathable mesh lining is made from 100% PET from recycled plastic bottles. 100% ...
    The slim, fashion-forward chukka silhouette of the Galen satisfies the dapper gentleman's need for smart design and comfort. This 3 ...
    UGG Galen Chukka Boot (Men's)
    Description:
    The slim, fashion-forward chukka silhouette of the Galen satisfies the dapper gentleman's need for smart design and comfort. This 3 eyelet chukka boot features distressed suede detail on the heel counter and pull tab. Insole: Dual density leather lined foam ...