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  1. Home
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Men's Sperry Boots 71 Products

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  • Boots (33)
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  • Leather (15)
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Featured Boots & Chukkas

 
  • Avenue Embossed Duck Boot, Olive/Brown, dynamic

    Men's Avenue Embossed Duck Boot

    Sale Price$98.96 Regular Price$109.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey/Black
    Olive/Brown
    Tan/Brown
  • Avenue Embossed Duck Boot, Tan/Brown, dynamic

    Men's Avenue Embossed Duck Boot

    Sale Price $109.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey/Black
    Olive/Brown
    Tan/Brown
  • Cold Bay Duck Boot w/ Thinsulate™, Tan/Brown, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price $119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan/Brown
    Taupe/Navy
  • Cold Bay Duck Boot w/ Thinsulate™, Taupe/Navy, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan/Brown
    Taupe/Navy
  • Cutwater Deck Boot, BLACK, dynamic

    Men's Cutwater Deck Boot

    Sale Price $89.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    BLACK
    BLUE
    GREY
  • Authentic Original PLUSHWAVE Lug Chukka, Tan, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale Price $129.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Brown
    Tan
    Taupe
  • Striper Storm Chukka Boot, Tan Suede, dynamic

    Men's Striper Storm Chukka Boot

    Sale Price$85.46 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black Leather
    Tan
    Tan Suede
  • Ice Bay Boot w/ Thinsulate™, Black/Tan, dynamic

    Men's Ice Bay Boot w/ Thinsulate™

    Sale Price$125.96 Regular Price$139.95
    Wishlist Added to Wishlist
    Quick Add
  • Gold Cup Authentic Original Lug Chukka, Black, dynamic

    Men's Gold Cup Authentic Original Lug Chukka

    Sale Price$166.46 Regular Price$184.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
  • Gold Cup Commodore PLUSHWAVE Chukka, Black, dynamic

    Men's Gold Cup Commodore PLUSHWAVE Chukka

    Sale Price$170.96 Regular Price$189.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Gold Cup Commodore PLUSHWAVE Chukka, Tan, dynamic

    Men's Gold Cup Commodore PLUSHWAVE Chukka

    Sale Price$170.96 Regular Price$189.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Oxblood, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale Price$179.96 Regular Price$199.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Bone
    Oxblood
    Rust
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Rust, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale Price$179.96 Regular Price$199.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Bone
    Oxblood
    Rust
  • Cold Bay Rubber Chelsea Boot, Navy, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price $94.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Brown
    Grey/Yellow
    Navy
    Olive
  • Ice Bay Tall Boot w/ Thinsulate™, Black, dynamic

    Men's Ice Bay Tall Boot w/ Thinsulate™

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Brown/Olive
  • Ice Bay Tall Boot w/ Thinsulate™, Brown/Olive, dynamic

    Men's Ice Bay Tall Boot w/ Thinsulate™

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Brown/Olive
  • Sperry x John Legend Authentic Original Vibram Lug Boot, Black, dynamic

    Men's Sperry x John Legend Authentic Original Vibram Lug Boot

    Sale Price$224.96 Regular Price$249.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Chestnut
  • Sperry x John Legend Authentic Original Vibram Lug Boot, Chestnut, dynamic

    Men's Sperry x John Legend Authentic Original Vibram Lug Boot

    Sale Price$224.96 Regular Price$249.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Chestnut
  • Striper Storm Boot, Brown, dynamic

    Men's Striper Storm Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
  • Cutwater Deck Boot, BLUE, dynamic

    Men's Cutwater Deck Boot

    Sale Price $89.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    BLACK
    BLUE
    GREY
  • Cutwater Deck Boot, GREY, dynamic

    Men's Cutwater Deck Boot

    Sale Price $89.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    BLACK
    BLUE
    GREY
  • Authentic Original PLUSHWAVE Lug Chukka, Brown, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale Price $129.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Brown
    Tan
    Taupe
  • Authentic Original PLUSHWAVE Lug Chukka, Black, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale Price $129.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Brown
    Tan
    Taupe
  • Avenue Embossed Duck Boot, Grey/Black, dynamic

    Men's Avenue Embossed Duck Boot

    Sale Price$98.96 Regular Price$109.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey/Black
    Olive/Brown
    Tan/Brown
  • Saltwater Nylon Duck Boot, Black, dynamic

    Men's Saltwater Nylon Duck Boot

    Sale Price$95.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Navy
  • Saltwater Nylon Duck Boot, Navy, dynamic

    Men's Saltwater Nylon Duck Boot

    Sale Price$103.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Navy
  • Saltwater Duck Boot, Black/Amaretto, dynamic

    Men's Saltwater Duck Boot

    Sale Price$89.96 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Saltwater Duck Boot, Brown/Coffee, dynamic

    Men's Saltwater Duck Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Saltwater Duck Boot, Brown/Navy, dynamic

    Men's Saltwater Duck Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Striper Storm Hiker Boot, Brown/Camo, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Authentic Original Tumbled Leather Boat Chukka, Dark Brown, dynamic

    Men's Authentic Original Tumbled Leather Boat Chukka

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Dark Brown
    Tan
  • Striper Storm Chukka Boot, Black Leather, dynamic

    Men's Striper Storm Chukka Boot

    Sale Price$85.46 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black Leather
    Tan
    Tan Suede
  • Striper Storm Chukka Boot, Tan, dynamic

    Men's Striper Storm Chukka Boot

    Sale Price$85.46 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black Leather
    Tan
    Tan Suede
  • Striper Storm Hiker Boot, Tan, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Authentic Original Tumbled Leather Boat Chukka, Tan, dynamic

    Men's Authentic Original Tumbled Leather Boat Chukka

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Dark Brown
    Tan
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Bone, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale Price$179.96 Regular Price$199.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Bone
    Oxblood
    Rust
  • Striper Storm Hiker Boot, Taupe, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Saltwater Duck Boot, Black/Black, dynamic

    Men's Saltwater Duck Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Saltwater Duck Boot, Tan/Caramel, dynamic

    Men's Saltwater Duck Boot

    Sale Price $99.95
    Wishlist Added to Wishlist
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Authentic Original Lug Chukka, Tan, dynamic

    Men's Authentic Original Lug Chukka

    Sale Price $149.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Amaretto
    Tan
  • Striper Storm Hiker Boot, Navy, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Seahiker Dinghy Boot, Grey, dynamic

    Men's Seahiker Dinghy Boot

    Sale Price $119.95
    Wishlist Added to Wishlist
    Quick Add
  • Cold Bay Rubber Chelsea Boot, Olive, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price $94.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Brown
    Grey/Yellow
    Navy
    Olive
  • Cold Bay Chukka w/ Thinsulate™, Brown/Coffee, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price $109.95
    Wishlist Added to Wishlist
    Quick Add
  • Authentic Original Lug Chukka, Amaretto, dynamic

    Men's Authentic Original Lug Chukka

    Sale Price $149.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Amaretto
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  • Moc-Sider Nylon Slip On, Blue, dynamic

    Men's Moc-Sider Nylon Slip On

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  • Striper Storm Hiker Boot, Black Multi, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
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  • Authentic Original Tumbled Lug Chukka, Black, dynamic

    Men's Authentic Original Tumbled Lug Chukka

    Sale Price$134.96 Regular Price$149.95
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Recommended Products

Men's Casual Boots

Be ready for any adventure – from the office park to the actual park – in men's chukka boots from Sperry. Our wide selection of men's casual boots is designed to keep you steady, comfortable and stylish wherever your journey takes you. From strolling on the beach, boardwalk or promenade to hailing a cab for your next big night out, your new men's chukka boots will stand up to the weather and stand out in the crowd. Our carefully crafted designs feature waterproof, seam-sealed construction, non-marking rubber outsoles, heavy lugs and Wave-Siping™ for the ultimate in wet/dry protection and traction, plus rawhide laces, premium leather accents and genuine, hand-sewn details for unbeatable charm. Classic Sperry styling ensures our men's chukka boots will help you handle any endeavor with confidence. From simple, slip-on and sneaker styles to high-top duck boots made to protect your every step, you're sure to find a Sperry chukka style you love. Whatever your next quest demands of you, keep comfortable men's casual boots from Sperry.

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