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

Styles & sizes will vary in-stores

Ankle Boots

Stylish, weather-ready women’s boots crafted for comfort and timeless appeal.
All Boots

All Boots

Ankle Boots

Ankle Boots

Tall Boots

Tall Boots

Combat Boots

Combat Boots

Hiking Boots

Hiking Boots

Rain Boots

Rain Boots

Western Boots

Western Boots

Wide Fit

Wide Fit

Winter

Winter

Sale

Sale

Compare (0/5)

319 products

Grahame James Women's Soho in Brown

Grahame James Women's Soho in Brown

$275.00 CAD
$275.00 CAD
Grahame James Women's Soho in Black

Grahame James Women's Soho in Black

$275.00 CAD
$275.00 CAD
Vagabond Women's Hedda in Chocolate

Vagabond Women's Hedda in Chocolate

$260.00 CAD
$260.00 CAD
Vagabond Women's Kelsey in Java

Vagabond Women's Kelsey in Java

$270.00 CAD
$270.00 CAD
Nine West Women's Ariza In Black M

Nine West Women's Ariza In Black M

$157.50 CAD
$157.50 CAD $225.00 CAD
Nine West Women's Reraye In Black M

Nine West Women's Reraye In Black M

$164.50 CAD
$164.50 CAD $235.00 CAD
Nine West Women's Reraye In Cognac67376/Ft M

Nine West Women's Reraye In Cognac67376/Ft M

$164.50 CAD
$164.50 CAD $235.00 CAD
Nine West Women's Reraye In Black/Dress

Nine West Women's Reraye In Black/Dress

$164.50 CAD
$164.50 CAD $235.00 CAD
Fitflop Women's F-Mode Chelsea in Black

Fitflop Women's F-Mode Chelsea in Black

$270.00 CAD
$270.00 CAD
Fitflop Women's F-Mode Chelsea in Mink Grey

Fitflop Women's F-Mode Chelsea in Mink Grey

$270.00 CAD
$270.00 CAD
Fitflop Women's F-MODE Stack Leather Chelsea Boots in All Black

Fitflop Women's F-MODE Stack Leather Chelsea Boots in All Black

$270.00 CAD
$270.00 CAD
Fitflop Women's IQ-COMFF Leather Zip Ankle Boots in All Black

Fitflop Women's IQ-COMFF Leather Zip Ankle Boots in All Black

$190.00 CAD
$190.00 CAD
Free People Women's Easy Does It Boot in Snake Combo

Free People Women's Easy Does It Boot in Snake Combo

From $120.00 CAD
From $120.00 CAD $240.00 CAD
Kenneth Cole Women's Salt Chelsea Boots in Black

Kenneth Cole Women's Salt Chelsea Boots in Black

$82.50 CAD
$82.50 CAD $165.00 CAD
Kenneth Cole Women's Salt Chelsea in Chocolate

Kenneth Cole Women's Salt Chelsea in Chocolate

$82.50 CAD
$82.50 CAD $165.00 CAD
La Canadienne Women's Delta in Black Suede

La Canadienne Women's Delta in Black Suede

$287.50 CAD
$287.50 CAD $575.00 CAD
La Canadienne Women's Delta in Caribou

La Canadienne Women's Delta in Caribou

$287.50 CAD
$287.50 CAD $575.00 CAD
La Canadienne Women's Siera in Black Leather

La Canadienne Women's Siera in Black Leather

$275.00 CAD
$275.00 CAD $550.00 CAD
La Canadienne Women's Siera in Brown Suede

La Canadienne Women's Siera in Brown Suede

$275.00 CAD
$275.00 CAD $550.00 CAD
Religious Comfort Women's Macdaddy in Black

Religious Comfort Women's Macdaddy in Black

$72.00 CAD
$72.00 CAD $144.00 CAD

Ankle Boots

Discover women’s ankle boots crafted for daily dressing. These versatile, easy-to-style booties pair with denim, dresses, trousers, and everything in between—making them an essential wardrobe staple season after season.

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

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

Customer Service

Mon-Fri, 9am-5pm EST.

Call Us

+1 (416) 367-4335

Get in Touch

info@heelboy.com
Home Cart Products