✌🏼 Free Shipping* on orders $150+ | Provincial exceptions may apply

Styles & sizes will vary in-stores

Men's Weatherproof Leather Shoes

For the man who takes on the day, rain or shine.
All Rain Ready

All Rain Ready

Rain Boots

Rain Boots

Rain Coats

Rain Coats

Waterproof Accessories

Waterproof Accessories

Waterproof Leather

Waterproof Leather

Waterproof Suede

Waterproof Suede

Umbrellas

Umbrellas

Compare (0/5)

52 products

Georgia Men's Gb00694 Short Boot Core 37 Wedge In Barracuda W

Georgia Men's Gb00694 Short Boot Core 37 Wedge In Barracuda W

$220.00 CAD
$220.00 CAD
Pajar Men's Fino in Black

Pajar Men's Fino in Black

$240.00 CAD
$240.00 CAD
Rocky Men's S2v Predator 8" Military Boot In Coyote M

Rocky Men's S2v Predator 8" Military Boot In Coyote M

$401.50 CAD
$401.50 CAD
Rocky Men's S2v 8" Waterproof 400G Insulated Military Bo In Coyote M

Rocky Men's S2v 8" Waterproof 400G Insulated Military Bo In Coyote M

$700.00 CAD
$700.00 CAD
Rocky Men's Core 8" Waterproof 800G Insulated Outdoor Bo In Brown M

Rocky Men's Core 8" Waterproof 800G Insulated Outdoor Bo In Brown M

$250.00 CAD
$250.00 CAD
Georgia Men's Gb00694 Short Boot Core 37 Wedge In Barracuda M

Georgia Men's Gb00694 Short Boot Core 37 Wedge In Barracuda M

$220.00 CAD
$220.00 CAD
UGG Men's Truckee Field Boot in Black

UGG Men's Truckee Field Boot in Black

$194.99 CAD
$194.99 CAD
UGG Men's Idyllwild Lace in Oak

UGG Men's Idyllwild Lace in Oak

$239.99 CAD
$239.99 CAD
Pajar Men's Fino in Ground Coffee

Pajar Men's Fino in Ground Coffee

$240.00 CAD
$240.00 CAD
UGG Men's Adirondack Boot XXV in Chestnut

UGG Men's Adirondack Boot XXV in Chestnut

$299.99 CAD
$299.99 CAD
UGG Men's Adirondack Boot XXV in Black

UGG Men's Adirondack Boot XXV in Black

$300.00 CAD
$300.00 CAD
Cougar Men's Aron In Chocolate M

Cougar Men's Aron In Chocolate M

$250.00 CAD
$250.00 CAD

Keen Men's Austin in Black

$200.00 CAD
$200.00 CAD
Keen Men's Targhee IV Mid Wp in Triple Black

Keen Men's Targhee IV Mid Wp in Triple Black

$230.00 CAD
$230.00 CAD

Keen Men's Hightrail Mid Wp in Brindle/Oak Buff

$200.00 CAD
$200.00 CAD
Keen Men's Revel IV Chelsea in Black/Black

Keen Men's Revel IV Chelsea in Black/Black

$230.00 CAD
$230.00 CAD
Keen Men's Austin in Chocolate Brown

Keen Men's Austin in Chocolate Brown

$200.00 CAD
$200.00 CAD
Keen Men's Revel IV High Polar in Canteen/Black

Keen Men's Revel IV High Polar in Canteen/Black

$260.00 CAD
$260.00 CAD
Keen Men's Targhee Ii Wp in Cascade Brown/Golden Yel

Keen Men's Targhee Ii Wp in Cascade Brown/Golden Yel

$200.00 CAD
$200.00 CAD
Keen Men's Targhee Ii Mid Wp in Black OlIVe/Yellow

Keen Men's Targhee Ii Mid Wp in Black OlIVe/Yellow

$220.00 CAD
$220.00 CAD

About Men's Weatherproof Leather Shoes

Weatherproof leather that doesn’t compromise on style—durable, comfortable, and ready for whatever the day throws at you.

Fast Delivery
14 Days Free Returns
Worldwide Shipping
Proudly Canadian
Secure Payment

Customer Service

Mon-Fri, 9am-5pm EST.

Call Us

+1 (416) 367-4335

Get in Touch

info@heelboy.com

FOLLOW US

<a href="https://www.instagram.com/heelboy/?hl=en" target="_blank" title="https://www.instagram.com/heelboy/?hl=en">@heelboy</a>

@heelboy

<a href="https://www.tiktok.com/@heelboyshoes" target="_blank" title="https://www.tiktok.com/@heelboyshoes">@heelboyshoes</a>

@heelboyshoes

Home Cart Products