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Blue short ankle boot rain boot

Rain Boots

Brown ankle boot with a black heel on a white background

Ankle Boots

Brown combat boot on grey background

Men's Boots

Cream key hole ballet flat on grey background

Flats

Brown men's penny loafer on grey background

Men's Loafers

Blue heel with embellished ankle strap on grey background

Heels

Black square toe flip flop on grey background

Sandals

grey retro lace up sneaker on grey background

Sneakers

Black and grey sneaker with N logo

Men's Sneakers

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
Black high-heeled shoe with a strap on a white background

Dolce Vita Women's Kamra Mesh in Onyx

$113.00 USD
$113.00 USD
Beige high-heeled sandal with a slingback strap on a white background

Dolce Vita Women's Kamra Mesh in Blush

$113.00 USD
$113.00 USD
White raffia bag with gold hardware on white background

Dolce Vita Women's Alice-R in Natural

$126.00 USD
$126.00 USD
Beige straw handbag with brown leather strap on a white background

Dolce Vita Women's Alice-R in Tan

$126.00 USD
$126.00 USD
Keen Women's Jasper in Silver Mink

Keen Women's Jasper in Silver Mink

$120.00 USD
$120.00 USD
Orange and black sneaker on a white background

Keen Women's Jasper Zionic in Cork/Java

$135.00 USD
$135.00 USD
Keen Women's Jasper in Pansy/Black

Keen Women's Jasper in Pansy/Black

$120.00 USD
$120.00 USD
Brown sneaker with blue laces on a white background

Keen Men's Jasper in Cathay Spice/Orion Blue

$120.00 USD
$120.00 USD
Frye & Co Women's Miranda14 In Dusty Rose M

Frye & Co Women's Miranda14 In Dusty Rose M

$180.00 USD
$180.00 USD
Frye & Co Women's Miranda Br In Banana M

Frye & Co Women's Miranda Br In Banana M

$195.00 USD
$195.00 USD
Frye & Co Women's Miranda14 In Taupe Cortez M

Frye & Co Women's Miranda14 In Taupe Cortez M

$165.00 USD
$165.00 USD
Frye & Co Women's Miranda14 In Dusty Blue M

Frye & Co Women's Miranda14 In Dusty Blue M

$180.00 USD
$180.00 USD

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Easy 14 Day Returns

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Fresh Styles for the Season WOMEN'S SPRING COLLECTION
Discover lightweight footwear, breathable styles, and vibrant new arrivals perfect for spring. From sandals to sneakers, refresh your wardrobe with our latest collection.
heel boy
New Arrivals This Season MEN'S SPRING COLLECTION
Explore fresh men's styles designed for spring—lightweight sneakers, breathable loafers, and versatile new arrivals that transition seamlessly from season to season.

Shop the Spring Edit

Ilse Jacobsen Women's Tulip139 in Mocca

Ilse Jacobsen Women's Tulip139 in Mocca

$94.00 USD
$94.00 USD
Ilse Jacobsen Women's Tulip139 in Army

Ilse Jacobsen Women's Tulip139 in Army

$94.00 USD
$94.00 USD
Ilse Jacobsen Women's Tulip3479 in Kit Pearled Ivory

Ilse Jacobsen Women's Tulip3479 in Kit Pearled Ivory

$124.00 USD
$124.00 USD
Ilse Jacobsen Women's Tulip3479 in Cashew Pearled Ivory

Ilse Jacobsen Women's Tulip3479 in Cashew Pearled Ivory

$124.00 USD
$124.00 USD
Alohas Women's TB. 490 Mule in Crochet Cream

Alohas Women's TB. 490 Mule in Crochet Cream

$274.00 USD
$274.00 USD
Gray sneaker with white sole on a white background

Alohas Women's TB. 490 Rife in Grey

$263.00 USD
$263.00 USD
Pink sneaker with red accents on a white background

Alohas Women's TB. 490 Rife in Sea Pink

$263.00 USD
$263.00 USD

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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