Skip to content
  • Free shipping on orders $50+

    • Australia
    • Canada
    • English
      French
    • Chile
    • Germany
    • Italy
    • Japan
    • Korea
    • Netherlands
    • Panamá
    • Philippines
    • Taiwan
    • Turkey
    • United Kingdom
    • United States
    Changing your country will empty your cart. By switching countries, some of the products, pricing, delivery, or promotions may be different.
    Ok
  • HELP
  • Guest User
  • Guest User Registered User
  • Guest User
  • Wishlist Wishlist
  • Order Status
    ORDER STATUS
    Chat
    CHAT
    Customer Service
    CUSTOMER SERVICE
    Exchange and Return
    RETURN
    Shipping Info
    SHIPPING INFO
    Site Feedback
    SITE FEEDBACK
  • Offers
Sperry logo Sperry
Sperry logo
  • Women
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Flats & Loafers
      • Mules
      • Slippers
      • Sandals & Flip flops
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Crest Vibe
      • Boat Shoe Lookbook

    Trending Now

    Women's Boots.

    Women's Boots

    Women's Cozy Styles.

    Cozy Styles

    Women's Saltwater Duck Boots.

    Saltwater Duck Boots

  • Men
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Herschel
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Loafers & Oxfords
      • Mules
      • Slippers
      • Sandals
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Striper II
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Boat Shoe Lookbook

    Trending Now

    Men's Boots.

    Men's Boots

    Men's Cozy Styles.

    Cozy Styles

    Men's Striper Storm.

    Striper Storm

  • Kids
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sale
    • Shop By
      • Big Kid (size 10.5 & up)
      • Little Kid (size 0-10)
      • Baby
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Sandals
    • Collections
      • Authentic Original
      • Saltwater Duck Boots
      • Easy On & Off
      • Boys' Shoes
      • Girls' Shoes
      • Washables
      • Uniform
    • Get Sizing Help

    Trending Now

    Kids' Boots

    Kids' Boots

    Kid's Cozy Styles

    Cozy Styles

  • SALE
    • Women's Sale
    • Men's Sale
    • Kids' Sale
    • New Markdowns
  • More...
    Women
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Flats & Loafers
      • Mules
      • Slippers
      • Sandals & Flip flops
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Crest Vibe
      • Boat Shoe Lookbook
    Men
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Herschel
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Loafers & Oxfords
      • Mules
      • Slippers
      • Sandals
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Striper II
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Boat Shoe Lookbook
    Kids
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sale
    • Shop By
      • Big Kid (size 10.5 & up)
      • Little Kid (size 0-10)
      • Baby
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Sandals
    • Collections
      • Authentic Original
      • Saltwater Duck Boots
      • Easy On & Off
      • Boys' Shoes
      • Girls' Shoes
      • Washables
      • Uniform
    • Get Sizing Help
    SALE
    • Women's Sale
    • Men's Sale
    • Kids' Sale
    • New Markdowns

Did you mean?

Products

Your Recent Searches

Popular Searches

Categories

Use your PayPal Account

Final Sale

Sizes and colors are limited and cannot be exchanged or returned

Flash Sale!

Enjoy extra 20% OFF sale

Use Code: SAVE20 > > > Shop Now

Top
  • Women
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Flats & Loafers
      • Mules
      • Slippers
      • Sandals & Flip flops
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Crest Vibe
      • Boat Shoe Lookbook
    • Shop Now
  • Men
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sperry x Herschel
      • Sperry x Pleasures
      • Online Exclusives
      • Sale
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Loafers & Oxfords
      • Mules
      • Slippers
      • Sandals
      • Sport
    • Collections
      • Authentic Original
      • Gold Cup
      • Saltwater Duck Boots
      • Duck Float Boots
      • Striper II
      • Plushwave
      • Moc-Sider Slip Ons
      • SeaCycled™
      • Cloud
      • Boat Shoe Lookbook
    • Shop Now
  • Kids
    • Favourites
      • New Arrivals
      • Best Sellers
      • Sale
    • Shop By
      • Big Kid (size 10.5 & up)
      • Little Kid (size 0-10)
      • Baby
    • Shoes
      • View All
      • Boat Shoes
      • Boots
      • Rain & Duck Boots
      • Sneakers
      • Sandals
    • Collections
      • Authentic Original
      • Saltwater Duck Boots
      • Easy On & Off
      • Boys' Shoes
      • Girls' Shoes
      • Washables
      • Uniform
    • Get Sizing Help
    • Shop Now
  • SALE
    • Women's Sale
    • Men's Sale
    • Kids' Sale
    • New Markdowns
    • Shop Now
  • Order Status HELP
    • Order Status
      ORDER STATUS
    • Chat
      CHAT
    • Customer Service
      CUSTOMER SERVICE
    • Exchange and Return
      RETURN
    • Shipping Info
      SHIPPING INFO
    • Site Feedback
      SITE FEEDBACK
  • Guest User Account
    Sign In Create an Account
  • Wishlist

Did you mean?

Products

Your Recent Searches

Popular Searches

Categories

Sperry Sperry
Cart  
Cart0
Top
Today's Offers

Click offer codes below to apply in checkout. Tap offer codes below to apply in checkout.

There are no promotions running at this time. There are no promotions running at this time.

Flash Sale! Enjoy extra 20% off sale with code SAVE20. Does not apply to past purchases and cannot be combined with any other $ or % offers. Coupon code required at checkout. Expires on February 5th 2023 at 11:45 pm.

Flash Sale!

Limited time only!

Enjoy extra 20% off sale

Use code: SAVE20

Shop Now
SAVE20
details

15% Off with code WELCOME-MCD-L5N-2G2. Offer valid at https://www.sperry.com/CA/en_CA/home on new email signups only. To redeem, shop now or reference your confirmation email to activate. Not valid on prior purchases, purchases at retail stores or other websites. Cannot be combined with any other offer. Excludes Sale.

Get 15% OFF your first order when you join our email list*

*excludes sale

Additional Benefits:

  • Be the first to hear about new products
  • Get exclusive offers and promotions

Email: Invalid email address

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

No Code Necessary
details
Feet in sneakers dangling off a boat.

BREAK OUT THE BOOTS

Once you step in, you're ready to step out.

View All Women Men Kids
  1. Home
  2. Men
  3. Shoes
  4. Boots

Men's Boots

41 Products
Filter

Filter By:

Filter

41 Products

Size/Width

Gender

  • Men's (41)

Size

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

Width

  • Medium (41)
  • Wide (6)
Colour
  • Black
  • Blue
  • Brown
  • Gray
  • Green
  • Red
  • Tan
Style
  • Boots (41)
  • Chukkas (11)
  • Duck Boots (19)
Material
  • Leather (5)
  • Suede (6)
  • Nylon (2)
  • Rubber (2)
  • Textile (1)
  • Vegan Leather (8)

Featured Boots

 
  • Sperry x Herschel Authentic Original™ Lug Chukka, Black, dynamic

    Men's Sperry x Herschel Authentic Original™ Lug Chukka

    Sale Price C$ 215.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Sperry x Herschel Authentic Original™ Lug Chukka, Tan, dynamic

    Men's Sperry x Herschel Authentic Original™ Lug Chukka

    Sale Price C$ 215.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Ice Bay 2° Boot, Black, dynamic

    Men's Ice Bay 2° Boot

    Sale PriceC$ 111.99 Regular PriceC$ 280.00
    Wishlist Added to Wishlist
    Quick Add
  • SeaCycled™ Ice Bay Boot, Taupe, dynamic

    Men's SeaCycled™ Ice Bay Boot

    Sale PriceC$ 75.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
  • Duck Float Lace Up Cozy Boot, Black, dynamic

    Men's Duck Float Lace Up Cozy Boot

    Sale PriceC$ 122.99 Regular PriceC$ 175.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Duck Float Lace Up Cozy Boot, Tan, dynamic

    Men's Duck Float Lace Up Cozy Boot

    Sale PriceC$ 122.99 Regular PriceC$ 175.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Authentic Original™ PLUSHWAVE™ Lug Chukka, Grey, dynamic

    Men's Authentic Original™ PLUSHWAVE™ Lug Chukka

    Sale PriceC$ 75.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
  • Duck Float Lace Up Boot, CAMO, dynamic

    Men's Duck Float Lace Up Boot

    Sale PriceC$ 97.99 Regular PriceC$ 140.00
    Wishlist Added to Wishlist
    Quick Add
  • Striper Storm Hiker Sneaker Boot, Black, dynamic

    Men's Striper Storm Hiker Sneaker Boot

    Sale Price C$ 150.00
    Wishlist Added to Wishlist
    Quick Add
  • SeaCycled™ Duck Float Zip Up Boot, BLACK, dynamic

    Men's SeaCycled™ Duck Float Zip Up Boot

    Sale Price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    BLACK
    KHAKI
    OLIVE
    RED
  • SeaCycled™ Duck Float Zip Up Boot, KHAKI, dynamic

    Men's SeaCycled™ Duck Float Zip Up Boot

    Sale Price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    BLACK
    KHAKI
    OLIVE
    RED
  • SeaCycled™ Duck Float Zip Up Boot, OLIVE, dynamic

    Men's SeaCycled™ Duck Float Zip Up Boot

    Sale Price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    BLACK
    KHAKI
    OLIVE
    RED
  • SeaCycled™ Duck Float Zip Up Boot, RED, dynamic

    Men's SeaCycled™ Duck Float Zip Up Boot

    Sale PriceC$ 89.99 Regular PriceC$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    BLACK
    KHAKI
    OLIVE
    RED
  • Authentic Original™ PLUSHWAVE™ Lug Chukka, Brown, dynamic

    Men's Authentic Original™ PLUSHWAVE™ Lug Chukka

    Sale PriceC$ 75.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Brown
    Taupe
  • Authentic Original™ PLUSHWAVE™ Lug Chukka, Taupe, dynamic

    Men's Authentic Original™ PLUSHWAVE™ Lug Chukka

    Sale Price C$ 170.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Brown
    Taupe
  • Moc-Sider Chukka, Black, dynamic

    Men's Moc-Sider Chukka

    Sale Price C$ 150.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Moc-Sider Chukka, Tan, dynamic

    Men's Moc-Sider Chukka

    Sale PriceC$ 59.99 Regular PriceC$ 150.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Cold Bay Duck Boot w/ Thinsulate™, Tan/Brown, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price C$ 180.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan/Brown
  • Cold Bay Rubber Chelsea Boot, Brown, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Brown
  • Saltwater Nylon Duck Boot, Navy, dynamic

    Men's Saltwater Nylon Duck Boot

    Sale PriceC$ 79.99 Regular PriceC$ 160.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Navy
  • Cold Bay Chukka w/ Thinsulate™, Brown/Coffee, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price C$ 160.00
    Wishlist Added to Wishlist
    Quick Add
  • Cold Bay Duck Boot w/ Thinsulate™, Taupe/Navy, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale PriceC$ 67.99 Regular PriceC$ 170.00
    Wishlist Added to Wishlist
    Quick Add
  • Saltwater Nylon Duck Boot, Black, dynamic

    Men's Saltwater Nylon Duck Boot

    Sale PriceC$ 79.99 Regular PriceC$ 160.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Navy
  • Saltwater Duck Boot, Brown/Coffee, dynamic

    Men's Saltwater Duck Boot

    Sale PriceC$ 89.99 Regular PriceC$ 180.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black/Black
    Brown/Coffee
    Brown/Navy
  • Cold Bay Rubber Chelsea Boot, Black, dynamic

    Men's Cold Bay Rubber Chelsea Boot

    Sale Price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    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
    Wishlist Added to Wishlist
    Quick Add
  • Saltwater Duck Boot, Black/Black, dynamic

    Men's Saltwater Duck Boot

    Sale PriceC$ 69.99 Regular PriceC$ 180.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black/Black
    Brown/Coffee
    Brown/Navy
  • Cold Bay Chukka w/ Thinsulate™, Black, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price C$ 160.00
    Wishlist Added to Wishlist
    Quick Add
  • Bahama Storm Boot, Black/Buffalo Check, dynamic

    Men's Bahama Storm Boot

    Sale PriceC$ 55.99 Regular PriceC$ 140.00
    Wishlist Added to Wishlist
    Quick Add
  • Cold Bay Duck Boot w/ Thinsulate™, Black, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price C$ 180.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan/Brown
  • Ice Bay Boot w/ Thinsulate™, Black/Tan, dynamic

    Men's Ice Bay Boot w/ Thinsulate™

    Sale PriceC$ 109.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
  • Saltwater Duck Boot, Brown/Navy, dynamic

    Men's Saltwater Duck Boot

    Sale PriceC$ 69.99 Regular PriceC$ 180.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black/Black
    Brown/Coffee
    Brown/Navy
  • Brewster Waterproof Duck Boot, Dark Tan, dynamic

    Men's Brewster Waterproof Duck Boot

    Sale Price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
  • Avenue Embossed Duck Boot, Grey/Black, dynamic

    Men's Avenue Embossed Duck Boot

    Sale PriceC$ 59.99 Regular PriceC$ 150.00
    Wishlist Added to Wishlist
    Quick Add
  • Gold Cup Authentic Original Lug Chukka, Black, dynamic

    Men's Gold Cup Authentic Original Lug Chukka

    Sale PriceC$ 99.99 Regular PriceC$ 250.00
    Wishlist Added to Wishlist
    Quick Add
  • Moc-Sider Shearling Chelsea Boot, Black, dynamic

    Men's Moc-Sider Shearling Chelsea Boot

    Sale PriceC$ 75.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Moc-Sider Shearling Chelsea Boot, Tan, dynamic

    Men's Moc-Sider Shearling Chelsea Boot

    Sale PriceC$ 75.99 Regular PriceC$ 190.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Cold Bay Chukka, Brown, dynamic

    Men's Cold Bay Chukka

    Sale Price C$ 160.00
    Wishlist Added to Wishlist
    Quick Add
  • Striper Storm Hiker Sneaker Boot, Grey, dynamic

    Men's Striper Storm Hiker Sneaker Boot

    Sale Price C$ 150.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Grey
    Tan
  • Striper Storm Hiker Sneaker Boot, Tan, dynamic

    Men's Striper Storm Hiker Sneaker Boot

    Sale Price C$ 150.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Grey
    Tan
  • Cold Bay Duck Boot, Brown, dynamic

    Men's Cold Bay Duck Boot

    Sale Price C$ 180.00
    Wishlist Added to Wishlist
    Quick Add

Filter By:

Filter

41 Products

Size/Width

Gender

  • Men's (41)

Size

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

Width

  • Medium (41)
  • Wide (6)
Colour
  • Black
  • Blue
  • Brown
  • Gray
  • Green
  • Red
  • Tan
Style
  • Boots (41)
  • Chukkas (11)
  • Duck Boots (19)
Material
  • Leather (5)
  • Suede (6)
  • Nylon (2)
  • Rubber (2)
  • Textile (1)
  • Vegan Leather (8)

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.

Footer Links

Get 15% Off
your first order*

You can unsubscribe at any time.
*Excludes sale styles.

This site is protected by reCAPTCHA and the
Google Privacy Policy and Terms of Service apply.

Privacy Policy

  • spotify
  • snapchat
  • youtube
  • twitter
  • pinterest
  • facebook
  • instagram
  • Supply Chain Transparency / Modern Slavery Act Disclosure
  • Terms & Conditions
  • Privacy Policy
  • Site Map

© Sperry.com. All rights reserved

Wolverine Worldwide Canada is located on the Treaty Lands and Territory of the Mississaugas of the Credit First Nation
and recognize this land as being home and traditional territory to other Indigenous people since time immemorial.

My Account

  • Sign In
  • Register
  • Order Status
  • Returns
  • Shipping Policy
  • Contact Us
  • 1-877-361-0080
  • Shopping Cart
  • Email Unsubscribe

Resources

  • Find a Store
  • Size Chart
  • Careers
  • Frequently Asked Questions

Popular Links

  • New Arrivals
  • Best Sellers
  • Boat Shoes
  • Authentic Originals

GET 15% OFF your first order*

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

You can unsubscribe at any time.
*Excludes sale styles.

Privacy Policy

Follow us

  • youtube
  • twitter
  • pinterest
  • facebook
  • instagram

You are viewing the Canada site

  • Australia
  • Canada
  • English
    French
  • Chile
  • Germany
  • Italy
  • Japan
  • Korea
  • Netherlands
  • Panamá
  • Philippines
  • Taiwan
  • Turkey
  • United Kingdom
  • United States
Changing your country will empty your cart. By switching countries, some of the products, pricing, delivery, or promotions may be different.
Ok
  • Australia
  • Canada
  • English
    French
  • Chile
  • Germany
  • Italy
  • Japan
  • Korea
  • Netherlands
  • Panamá
  • Philippines
  • Taiwan
  • Turkey
  • United Kingdom
  • United States
Changing your country will empty your cart. By switching countries, some of the products, pricing, delivery, or promotions may be different.
Ok
© 2022 SPERRY ALL RIGHTS RESERVED
  • Site Map
  • Privacy Policy
  • Terms & Conditions
  • Supply Chain Transparency / Modern Slavery Act Disclosure