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Ankle Boots

Ankle Boots

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Tall Boots

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Men's Boots

Women's Loafers

Women's Loafers

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Men's Loafers

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Women's Sneakers

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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

 Shop now
Frye & Co Women's Miranda14 In Dusty Rose M

Frye & Co Women's Miranda14 In Dusty Rose M

$239.00 CAD
$239.00 CAD
Frye & Co Women's Miranda Br In Banana M

Frye & Co Women's Miranda Br In Banana M

$259.00 CAD
$259.00 CAD
Frye & Co Women's Miranda14 In Taupe Cortez M

Frye & Co Women's Miranda14 In Taupe Cortez M

$219.00 CAD
$219.00 CAD
Frye & Co Women's Miranda14 In Dusty Blue M

Frye & Co Women's Miranda14 In Dusty Blue M

$239.00 CAD
$239.00 CAD
Floof Unisex Irish Goodbye Slogan Cap in Beige

Floof Unisex Irish Goodbye Slogan Cap in Beige

$35.00 CAD
$35.00 CAD
Floof Unisex Clover Icon Cap in Beige

Floof Unisex Clover Icon Cap in Beige

$35.00 CAD
$35.00 CAD
Floof Unisex Clover Icon Cap in Black

Floof Unisex Clover Icon Cap in Black

$35.00 CAD
$35.00 CAD
Floof Unisex Clover Icon Cap in White

Floof Unisex Clover Icon Cap in White

$35.00 CAD
$35.00 CAD
New Balance Unisex 204L in Rosewood/Pink Salt

New Balance Unisex 204L in Rosewood/Pink Salt

$154.99 CAD
$154.99 CAD
New Balance Unisex 204L in Sea Salt/Linen

New Balance Unisex 204L in Sea Salt/Linen

$154.99 CAD
$154.99 CAD
New Balance Unisex 204L in Silver Metallic/Double Bubble

New Balance Unisex 204L in Silver Metallic/Double Bubble

$154.99 CAD
$154.99 CAD
New Balance Unisex 204L in Timberwolf

New Balance Unisex 204L in Timberwolf

$154.99 CAD
$154.99 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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