This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

info@heelboy.com (416) 367-4335

RECEIVE A $15 GIFT VOUCHER WITH ANY PURCHASE

Styles & sizes will vary in-stores

Men's Boots

From durable waterproof boots to sleek chukka boots, we what you're looking for.

Men's Chelsea Boots
Chelsea Boots
Men's Chukka Boots
Chukka Boots
Men's Hiking Boots
Hiking Boots
Men's Rain & Waterproof Shoes
Rain & Waterproof
Men's Winter Boots
Winter Boots

Filters

Price
 
 
 
$
-
$
Size
More options
Product type
Brand
More options
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W
Wider Fit

Durango Men's Maverick Xp S 11 Work Western Boot Maverick Xp Brown W

$300.00 CAD
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M

Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown M

$315.00 CAD
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W
Wider Fit

Durango Men's Maverick Xp S 11 In Waterproof Work Boot Maverick Xp Brown W

$315.00 CAD
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M

Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown M

$295.00 CAD
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W
Wider Fit

Durango Men's Maverick Xp S 11 In Work Boot Maverick Xp Brown W

$295.00 CAD
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M
Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M

Durango Men's Rebel S 12 In Waterproof Western Boot Rebel Brown M

$295.00 CAD
 
 Wider Fit

Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black W

$295.00 CAD
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Durango Men's Rebel S 12 Western Boot Rebel Brown W
Wider Fit

Durango Men's Rebel S 12 Western Boot Rebel Brown W

$295.00 CAD
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M
Durango Men's Rebel S 12 Western Boot Rebel Brown M

Durango Men's Rebel S 12 Western Boot Rebel Brown M

$295.00 CAD
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee
Wider Fit

Durango Men's Arena Pro Wos 13 In Western Boot Arena Pro Black Ee

$400.00 CAD
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M
Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M

Durango Men's Maverick Xp S 11 In Ventilated Work Boot Maverick Xp Brown M

$300.00 CAD
Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W
Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W
Wider Fit

Durango Men's Maverick Xp 'S 11"Ventilated Western Work Boot Maverick Xp Brown W

$290.00 CAD
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M

Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Black M

$295.00 CAD
 
 Wider Fit

Durango Men's Rebel S 12 In Western Boot Rebel Brown Ee

$250.00 CAD
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M

Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown M

$315.00 CAD
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown W
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown W
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown W
Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown W
Wider Fit

Durango Men's Rebel Pro 'S 12" Western Boot Rebel Pro Brown W

$315.00 CAD
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M

Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown M

$295.00 CAD
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W
Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W
Wider Fit

Durango Men's Rebel Frontier S 12 In Western Boot Durango Rebel Frontier Brown W

$295.00 CAD
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M
Durango Men's Shyloh S 12 In Western Boot Shyloh Black M

Durango Men's Shyloh S 12 In Western Boot Shyloh Black M

$225.00 CAD
Durango Men's Shyloh S 12 In Western Boot Shyloh Brown M
Durango Men's Shyloh S 12 In Western Boot Shyloh Brown M
Durango Men's Shyloh S 12 In Western Boot Shyloh Brown M

Durango Men's Shyloh S 12 In Western Boot Shyloh Brown M

$245.00 CAD
 

Durango Men's Rebel S 12 In Western Boot Rebel Brown D

$250.00 CAD
ECCO Men's ULT-TRN Mid WP in Black/Black
ECCO Men's ULT-TRN Mid WP in Black/Black
ECCO Men's ULT-TRN Mid WP in Black/Black

ECCO Men's ULT-TRN Mid WP in Black/Black

$250.00 CAD
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown

Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Dark Brown

$300.00 CAD
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black
Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black

Palladium Men's Pallatrooper Hkr WP+ X Finisterre in Black

$300.00 CAD