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Ankle Boots

Ankle Boots

Tall Boots

Tall Boots

Men's Boots

Men's Boots

Women's Loafers

Women's Loafers

Men's Loafers

Men's Loafers

Women's Sneakers

Women's Sneakers

Men's Sneakers

Men's Sneakers

Men's Winter

Men's Winter

Women's Winter

Women's Winter

heel boy
Female-founded Canadian boutique est. 1998

Curated Style, Trusted for 25+ Years

Discover carefully selected pieces from premium brands, chosen with the expertise that comes from over two decades in fashion.

 Shop Pre-Spring Edit

Explore Our Favourites

Handpicked styles our customers can't get enough of
Pajar Women's Montreal in Black

Pajar Women's Montreal in Black

$225.00 CAD
$225.00 CAD
Pajar Women's Montreal in Cognac

Pajar Women's Montreal in Cognac

$225.00 CAD
$225.00 CAD
Grahame James Women's Soho in Black

Grahame James Women's Soho in Black

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

Grahame James Women's Soho in Brown

$275.00 CAD
$275.00 CAD
Ilse Jacobsen Women's Tulip Platform in White

Ilse Jacobsen Women's Tulip Platform in White

$125.00 CAD
$125.00 CAD
Ilse Jacobsen Women's Tulip Platform in Black

Ilse Jacobsen Women's Tulip Platform in Black

$125.00 CAD
$125.00 CAD
Ilse Jacobsen Women's Tulip139 in Black

Ilse Jacobsen Women's Tulip139 in Black

$120.00 CAD
$120.00 CAD
Ilse Jacobsen Women's Tulip in Kit

Ilse Jacobsen Women's Tulip in Kit

From $60.00 CAD
From $60.00 CAD $120.00 CAD
UGG Women's Classic Mini Platform in Chestnut

UGG Women's Classic Mini Platform in Chestnut

$200.00 CAD
$200.00 CAD
UGG Women's Classic Ultra Mini in Chestnut

UGG Women's Classic Ultra Mini in Chestnut

$185.00 CAD
$185.00 CAD
UGG Women's Classic Ultra Mini in Black

UGG Women's Classic Ultra Mini in Black

$185.00 CAD
$185.00 CAD
UGG Women's Elea Slip-On in Dusted Cocoa

UGG Women's Elea Slip-On in Dusted Cocoa

$150.00 CAD
$150.00 CAD

Free Shipping over $150*

Shipping Policy

Easy 14 Day Returns

Return Policy

Free In-Store Pick Ups

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Canadian-Owned for Over 25 Years

Our Story

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Cold-Weather Essentials WOMEN'S WINTER COLLECTION
From insulated boots to cozy scarves and gloves, find everything you need to take on winter in comfort and style.
heel boy
Gear Up for the Cold MEN'S WINTER COLLECTION
Explore men's winter boots and essentials designed for warmth, traction, and everyday versatility.
Ugg Women's Adirondack Boot Tall Iii in Chestnut

Ugg Women's Adirondack Boot Tall Iii in Chestnut

$375.00 CAD
$375.00 CAD
UGG Women's Adirondack III Tall Boot in Black Black

UGG Women's Adirondack III Tall Boot in Black Black

$375.00 CAD
$375.00 CAD
Ugg Women's Adirondack Boot Iii in Black/Black

Ugg Women's Adirondack Boot Iii in Black/Black

$300.00 CAD
$300.00 CAD
UGG Women's Adirondack III in Chestnut

UGG Women's Adirondack III in Chestnut

$300.00 CAD
$300.00 CAD
Pajar Women's Harrow in Sand

Pajar Women's Harrow in Sand

$330.00 CAD
$330.00 CAD
Pajar Women's Galaxy in Rose Gold

Pajar Women's Galaxy in Rose Gold

$200.00 CAD
$200.00 CAD
Pajar Women's Galaxy Lama in Beige

Pajar Women's Galaxy Lama in Beige

$225.00 CAD
$225.00 CAD

Happy Feet, Happy Customers:

"Love shopping at Heel boy

Super seamless finding exactly what I was looking for and getting to me quickly"

Rebecca K.

"Excellent customer service and easy exchange"

Hervé L.

"Easy purchase. Fast delivery and quality shoes. Glad I found Heel Boy and they are local too."

Bonnie F.

"Fabulous way to find shoes and the service was wonderful"

Jeannette B.

"Highly recommend this store!

I bought a pair of shoes for my wedding and I absolutely love them...The quality is great and the delivery was fast..."

Svitlana S.

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Customer Service

Mon-Fri, 9am-5pm EST.

Call Us

+1 (416) 367-4335

Get in Touch

info@heelboy.com
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