Skip to content

Official website. Shop with confidence.

Free shipping

Conditions apply
In-store pickup

For some locations
Easy returns

Hassle free returns policy
Proudly Canadian

Family owned and operated

🔖 EXTRA $10 OFF SALE! Check exclusive offers. (Only this weekend August 1st to 3rd). Shop Now!

Search

Menu

New Arrivals
Shop by Brand
- Shop by Brand
- Featured Brands
  
  Aetrex
  Birkenstock
  Clarks
  Ecco
  Michael Kors
  New Balance
  Vessi
- A
  
  Aetrex
  Allrounder
  Anzia
  Ara
  Arctic Mukluk
- B
  
  Birkenstock
  Blondo
  Blundstone
  Bogs
  BootRescue
- C
  
  Canada Comfort
  Clarks
  Cobb Hill
  Cole Haan
  Collexion Italy
- D
  
  Dansko
  Dunham
- E
  
  Ecco
- F
  
  Finn Comfort
  FitFlop
  Foamtreads
- G
  
  Gabor
  Glerups
- H
  
  Haflinger
  Hotsox
  Hunter Boots
- I
  
  Italian Comfort
- J
  
  Johnston & Murphy
  Josef Seibel
- K
  
  Keds
  Keen
- L
  
  Lady Comfort
  Lady Diana
- M
  
  Mephisto
  Merrell
  Michael Kors
- N
  
  Naot
  NEXGRIP
  New Balance
- O
  
  Olang
  Ortho Flex
  Outlander
- P
  
  Pajar
  Palladium
  Papillio
  Piccadilly
- R
  
  Redback
  Remonte
  Rieker
  Rockport
  Romika
- S
  
  Sabatini
  SAS Shoes
  Simcan Socks
  Sperry
  Stefania Italy
- T
  
  Taos
  Timberland
  Toe Warmers
  Toni Pons
  Travelon
- V
  
  Vessi
  Volant James
- W
  
  Wanderlust
  Wonders
  Wonder Walk
- Shop All Brands
Women's
Men's
Unisex
Accessories
Sale

Find a Store

Home
Men's Winter Boot

Men's Winter Boot

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

FiltersFilter & Sort

Applied Filters

Clear all

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

Colour

Black (23)
Brown (3)
Grey (1)
Navy (1)
Red (1)
Tan (1)

Clear

Gender

Men (22)
Unisex (8)

Clear

Size

Clear

Brand

Blundstone (6)
Merrell (1)
NEXGRIP (1)
Olang (8)
Pajar (5)
Rieker (4)
Toe Warmers (3)
Wanderlust (2)

Clear

Width

Extra Wide (4)
Wide (3)

Clear

Price

From $

-

To $

From To

Clear

Shoe Type

Boots (2)
Hiking (2)
Winter Boots (26)

Clear

Waterproof

No (3)
Yes (26)

Clear

Sale
05173 Men's Boot
Rieker

1 review

From $119.99 ~~$155.00~~
Toe Warmers Men's Albert Flip Grip Extra Wide Waterproof Boot
Toe Warmers

No reviews

$250.00
Rieker 03660 Men's Zip Up Ankle Boot in Black
Rieker

No reviews

$170.00
F8301 Men's Lace Up Boot
Rieker

1 review

$220.00
Blundstone 2081 Winter Thermal Dress Boot
Blundstone

No reviews

$300.00
Olang Kursk Men's Boots
Olang

No reviews

$299.00
Sale
Olang Kiev Men's Boots
Olang

1 review

From $259.99 ~~$285.00~~
Wanderlust Jacob Men's Side Zip Commuter Boot
Wanderlust

No reviews

$120.00
Wanderlust Tony Men's Velcro Boot
Wanderlust

No reviews

$120.00
Rieker 37770 Men's Zip Up Ankle Boot in Black
Rieker

No reviews

$160.00
Austin Men's Boot
Pajar

No reviews

$250.00
Sale
Sale

Sale

Olang Spider Unisex Vibram Hiking Boots
Olang

1 review

$199.99 ~~$285.00~~
Olang Tatra Men's Boots
Olang

No reviews

$290.00
Sale
Sale

Sale

Olang Spider Unisex Vibram Hiking Boots in Antracite
Olang

1 review

$199.99 ~~$285.00~~
Men's Coldpack 3 Thermo Tall Zip Waterproof
Merrell

No reviews

$260.00
Blundstone 566 Winter Waterproof Unisex Boot
Blundstone

No reviews

$300.00

Showing 16 of 30

Your cart

Your cart is empty

Subtotal:$0.00 CAD

Loading...

Who we are

Walking on a Cloud is a Canadian family owned and operated business. We are committed to and take pride in constantly exceeding our customers' expectations.

Facebook
Instagram

Company Info

About Us
Store Locations
Career Opportunities
Privacy Policy
Shipping Policy
Return Policy
Contact Us

Shop Now

Brands
New Arrivals
Women's Shoes
Men's Shoes
Unisex Shoes
Shoe Accessories
Blog

Newsletter

Sign up for exclusive offers, original stories, events and more.

Email

Payment methods accepted

© 2026 Walking On a Cloud. Powered by Shopify