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Sperry Boots

WEATHER OR NOT

Ever-ready tech. Everyday style. If the season brings it, our boots can take it.

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Boots 45 Products

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45 Products

Size/Width

Gender

  • Men's (45)

Size

  • 7
  • 7.5
  • 8
  • 8.5
  • 9
  • 9.5
  • 10
  • 10.5
  • 11
  • 11.5
  • 12
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  • 14
  • 15

Width

  • Medium (45)
Colour
  • Black
  • Blue
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  • White
Style
  • Slip Ons (3)
  • Boots (28)
  • Rain Boots (2)
  • Chukkas (5)
  • Duck Boots (12)
Material
  • Leather (11)
  • Suede (15)
  • Nylon (3)
  • Rubber (20)

Featured Boots

 
  • Bahama Storm Boot, Tan Leather, dynamic

    Men's Bahama Storm Boot

    Sale PriceC$ 76.99 Regular PriceC$ 140.00
    Quick Add
  • Striper Storm Boot, Tan Suede, dynamic

    Men's Striper Storm Boot

    Sale PriceC$ 79.99 Regular PriceC$ 140.00
    Quick Add
    2 Colors
    Grey Suede
    Tan Suede
  • Cold Bay Duck Boot w/ Thinsulate™, Taupe/Navy, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale PriceC$ 93.99 Regular PriceC$ 170.00
    Quick Add
    2 Colors
    Tan/Brown
    Taupe/Navy
  • Sperry x John Legend Authentic Original Vibram Lug Boot, Chestnut, dynamic

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

    Sale PriceC$ 215.99 Regular PriceC$ 360.00
    Quick Add
    2 Colors
    Black
    Chestnut
  • Cold Bay Rubber Chelsea Boot, Black, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price C$ 120.00
    Quick Add
    3 Colors
    Black
    Brown
    Olive
  • Bahama Storm Boot, Black/Buffalo Check, dynamic

    Men's Bahama Storm Boot

    Sale PriceC$ 79.99 Regular PriceC$ 140.00
    Quick Add
  • Saltwater Duck Boot, Black/Amaretto, dynamic

    Men's Saltwater Duck Boot

    Sale PriceC$ 87.99 Regular PriceC$ 160.00
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Ice Bay Boot w/ Thinsulate™, Navy/Tan, dynamic

    Men's Ice Bay Boot w/ Thinsulate™

    Sale PriceC$ 94.99 Regular PriceC$ 190.00
    Quick Add
  • Avenue Embossed Duck Boot, Grey/Black, dynamic

    Men's Avenue Embossed Duck Boot

    Sale PriceC$ 82.99 Regular PriceC$ 150.00
    Quick Add
    2 Colors
    Grey/Black
    Tan/Brown
  • Cold Bay 3-Eye Boot w/ Thinsulate™, Brown/Tan, dynamic

    Men's Cold Bay 3-Eye Boot w/ Thinsulate™

    Sale Price C$ 140.00
    Quick Add
  • Moc-Sider Buffalo Check Slip On, Grey Plaid, dynamic

    Men's Moc-Sider Buffalo Check Slip On

    Sale PriceC$ 49.99 Regular PriceC$ 90.00
    Quick Add
    3 Colors
    Blue Plaid
    Grey Plaid
    Red Plaid
  • Ice Bay Tall Boot w/ Thinsulate™, Brown/Olive, dynamic

    Men's Ice Bay Tall Boot w/ Thinsulate™

    Sale Price C$ 220.00
    Quick Add
    2 Colors
    Black
    Brown/Olive
  • Striper Storm Hiker Boot, Tan, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price C$ 140.00
    Quick Add
    5 Colors
    Black Multi
    Brown/Camo
    Grey
    Tan
    Taupe
  • Ice Bay Tall Boot w/ Thinsulate™, Black, dynamic

    Men's Ice Bay Tall Boot w/ Thinsulate™

    Sale PriceC$ 120.99 Regular PriceC$ 220.00
    Quick Add
    2 Colors
    Black
    Brown/Olive
  • Cold Bay Rubber Chelsea Boot, Brown, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price C$ 120.00
    Quick Add
    3 Colors
    Black
    Brown
    Olive
  • Authentic Original PLUSHWAVE Lug Chukka, Taupe, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale PriceC$ 127.99 Regular PriceC$ 170.00
    Quick Add
    3 Colors
    Black
    Brown
    Taupe
  • Saltwater Duck Boot, Black/Black, dynamic

    Men's Saltwater Duck Boot

    Sale Price C$ 160.00
    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 C$ 160.00
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Seahiker Dinghy Boot, Grey, dynamic

    Men's Seahiker Dinghy Boot

    Sale Price C$ 160.00
    Quick Add
  • Cutwater Deck Boot, GREY, dynamic

    Men's Cutwater Deck Boot

    Sale Price C$ 120.00
    Quick Add
    2 Colors
    BLACK
    GREY
  • Striper Storm Hiker Boot, Grey, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price C$ 140.00
    Quick Add
    5 Colors
    Black Multi
    Brown/Camo
    Grey
    Tan
    Taupe
  • Saltwater Duck Boot, Tan/Caramel, dynamic

    Men's Saltwater Duck Boot

    Sale PriceC$ 87.99 Regular PriceC$ 160.00
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Authentic Original PLUSHWAVE Lug Chukka, Brown, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale Price C$ 170.00
    Quick Add
    3 Colors
    Black
    Brown
    Taupe
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Oxblood, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale PriceC$ 139.99 Regular PriceC$ 280.00
    Quick Add
    2 Colors
    Bone
    Oxblood
  • Sperry x Herschel Authentic Original Vibram Chukka, Navy, dynamic

    Men's Sperry x Herschel Authentic Original Vibram Chukka

    Sale PriceC$ 239.99 Regular PriceC$ 300.00
    Quick Add
    2 Colors
    Brown
    Navy
  • Striper Storm Boot, Grey Suede, dynamic

    Men's Striper Storm Boot

    Sale PriceC$ 79.99 Regular PriceC$ 140.00
    Quick Add
    2 Colors
    Grey Suede
    Tan Suede
  • Authentic Original PLUSHWAVE Lug Chukka, Black, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale PriceC$ 127.99 Regular PriceC$ 170.00
    Quick Add
    3 Colors
    Black
    Brown
    Taupe
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Bone, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale PriceC$ 134.99 Regular PriceC$ 280.00
    Quick Add
    2 Colors
    Bone
    Oxblood
  • Sperry x John Legend Authentic Original Vibram Lug Boot, Black, dynamic

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

    Sale PriceC$ 249.99 Regular PriceC$ 360.00
    Quick Add
    2 Colors
    Black
    Chestnut
  • Cutwater Deck Boot, BLACK, dynamic

    Men's Cutwater Deck Boot

    Sale Price C$ 120.00
    Quick Add
    2 Colors
    BLACK
    GREY
  • Sperry x Herschel Authentic Original Vibram Chukka, Brown, dynamic

    Men's Sperry x Herschel Authentic Original Vibram Chukka

    Sale PriceC$ 239.99 Regular PriceC$ 300.00
    Quick Add
    2 Colors
    Brown
    Navy
  • Cold Bay Chukka w/ Thinsulate™, Brown/Coffee, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price C$ 150.00
    Quick Add
  • Striper Storm Boot, Brown, dynamic

    Men's Striper Storm Boot

    Sale PriceC$ 79.99 Regular PriceC$ 140.00
    Quick Add
  • Moc-Sider Buffalo Check Slip On, Red Plaid, dynamic

    Men's Moc-Sider Buffalo Check Slip On

    Sale PriceC$ 59.99 Regular PriceC$ 90.00
    Quick Add
    3 Colors
    Blue Plaid
    Grey Plaid
    Red Plaid
  • Striper Storm Hiker Boot, Brown/Camo, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price C$ 140.00
    Quick Add
    5 Colors
    Black Multi
    Brown/Camo
    Grey
    Tan
    Taupe
  • Cold Bay Chukka w/ Thinsulate™, Black, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price C$ 150.00
    Quick Add
  • Cold Bay Duck Boot w/ Thinsulate™, Tan/Brown, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price C$ 170.00
    Quick Add
    2 Colors
    Tan/Brown
    Taupe/Navy
  • Saltwater Duck Boot, Brown/Coffee, dynamic

    Men's Saltwater Duck Boot

    Sale Price C$ 160.00
    Quick Add
    5 Colors
    Black/Amaretto
    Black/Black
    Brown/Coffee
    Brown/Navy
    Tan/Caramel
  • Avenue Embossed Duck Boot, Tan/Brown, dynamic

    Men's Avenue Embossed Duck Boot

    Sale PriceC$ 82.99 Regular PriceC$ 150.00
    Quick Add
    2 Colors
    Grey/Black
    Tan/Brown
  • Striper Storm Hiker Boot, Taupe, dynamic

    Men's Striper Storm Hiker Boot

    Sale PriceC$ 64.99 Regular PriceC$ 140.00
    Quick Add
    5 Colors
    Black Multi
    Brown/Camo
    Grey
    Tan
    Taupe
  • Brewster Waterproof Duck Boot, Dark Tan, dynamic

    Men's Brewster Waterproof Duck Boot

    Sale Price C$ 140.00
    Quick Add
  • Moc-Sider Buffalo Check Slip On, Blue Plaid, dynamic

    Men's Moc-Sider Buffalo Check Slip On

    Sale PriceC$ 44.99 Regular PriceC$ 90.00
    Quick Add
    3 Colors
    Blue Plaid
    Grey Plaid
    Red Plaid
  • Gold Cup Authentic Original Lug Chukka, Black, dynamic

    Men's Gold Cup Authentic Original Lug Chukka

    Sale PriceC$ 124.99 Regular PriceC$ 250.00
    Quick Add
  • Striper Storm Hiker Boot, Black Multi, dynamic

    Men's Striper Storm Hiker Boot

    Sale PriceC$ 64.99 Regular PriceC$ 140.00
    Quick Add
    5 Colors
    Black Multi
    Brown/Camo
    Grey
    Tan
    Taupe
  • Striper Storm Chukka Boot, Tan, dynamic

    Men's Striper Storm Chukka Boot

    Sale PriceC$ 76.99 Regular PriceC$ 140.00
    Quick Add

Filter By:

Filter

45 Products

Size/Width

Gender

  • Men's (45)

Size

  • 7
  • 7.5
  • 8
  • 8.5
  • 9
  • 9.5
  • 10
  • 10.5
  • 11
  • 11.5
  • 12
  • 13
  • 14
  • 15

Width

  • Medium (45)
Colour
  • Black
  • Blue
  • Brown
  • Gray
  • Red
  • Tan
  • White
Style
  • Slip Ons (3)
  • Boots (28)
  • Rain Boots (2)
  • Chukkas (5)
  • Duck Boots (12)
Material
  • Leather (11)
  • Suede (15)
  • Nylon (3)
  • Rubber (20)

Recommended Products

Men's Chukka Boots

Dare to discover unexpected experiences and epic adventures with footwear that takes you from the boardwalk to the beach in comfort. Sperry mens ankle-height chukka boots are a go-to choice for keeping your feet warm and dry as you embark on your day-to-day adventures in cooler weather. Sperry chukka boots are available in a diverse array of colors and designs, including waterproof and winter-ready lined options. Each quality pair of Sperry chukkas is made to withstand the elements, with select styles featuring details like waterproof construction, gusseted tongues for protection from the elements, Wave-Siping for excellent traction on wet and dry conditions, and hand-sewn Tru-Moc construction. Wherever your day's explorations may take you, stay comfortable and stylish with mens Sperry chukka boots on your feet.

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