This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

info@heelboy.com (416) 367-4335

FREE GIFT WITH PURCHASE 🎁 All orders $150+ select gift in cart

Already on your phone? Shop on our App 📲

SAVE UP TO 70% OFF*

UNBOX THE SAVINGS

SHOP SALE

*EXCLUSIONS APPLY | IN-STORE AND ONLINE MAY DIFFER | ALL SALE ITEMS ARE FINAL SALE

  • ALL SALE
  • UNDER $100
  • SALE BOOTS
  • SALE HEELS
  • MEN'S SALE
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Sale

Vagabond Women's Eyra in Black

$269.50 CAD $385.00 CAD
Vagabond Women's Eyra in Mud
Vagabond Women's Eyra in Mud
Vagabond Women's Eyra in Mud
Sale

Vagabond Women's Eyra in Mud

$269.50 CAD $385.00 CAD
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Sale

Vagabond Women's Daniella in Black

$325.50 CAD $465.00 CAD
Vagabond Women's Alina in Black
Sale

Vagabond Women's Alina in Black

$189.00 CAD $270.00 CAD
Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Gold
Sale

Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Gold

$59.40 CAD $99.00 CAD
Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Black
Sale

Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Black

$59.40 CAD $99.00 CAD
Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Silver
Sale

Badgley Mischka Women's Dakota Sparkle Jacquard Envelope in Silver

$59.40 CAD $99.00 CAD
Badgley Mischka Women's Alicia Satin Envelope Clutch in Ivory
Sale

Badgley Mischka Women's Alicia Satin Envelope Clutch in Ivory

$59.40 CAD $99.00 CAD
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Vagabond Women's Eyra in Black
Sale

Vagabond Women's Eyra in Black

$269.50 CAD $385.00 CAD
Vagabond Women's Eyra in Mud
Vagabond Women's Eyra in Mud
Vagabond Women's Eyra in Mud
Sale

Vagabond Women's Eyra in Mud

$269.50 CAD $385.00 CAD
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Vagabond Women's Daniella in Black
Sale

Vagabond Women's Daniella in Black

$325.50 CAD $465.00 CAD
Vagabond Women's Aino in Black
Vagabond Women's Aino in Black
Sale

Vagabond Women's Aino in Black

$180.00 CAD $260.00 CAD
Marc Fisher Women's Hadya White M
Marc Fisher Women's Hadya White M
Marc Fisher Women's Hadya White M
Marc Fisher Women's Hadya White M
Sale

Marc Fisher Women's Hadya White M

$98.00 CAD $140.00 CAD
Marc Fisher Women's Hadya Red M
Marc Fisher Women's Hadya Red M
Marc Fisher Women's Hadya Red M
Marc Fisher Women's Hadya Red M
Sale

Marc Fisher Women's Hadya Red M

$98.00 CAD $140.00 CAD
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Marc Fisher Women's Lynnie in Back
Sale

Marc Fisher Women's Lynnie in Back

$192.00 CAD $240.00 CAD
Marc Fisher Women's Lynnie in Dark Red
Marc Fisher Women's Lynnie in Dark Red
Marc Fisher Women's Lynnie in Dark Red
Marc Fisher Women's Lynnie in Dark Red
Marc Fisher Women's Lynnie in Dark Red
Marc Fisher Women's Lynnie in Dark Red
Sale

Marc Fisher Women's Lynnie in Dark Red

$192.00 CAD $240.00 CAD
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Gola Men's Tennis Mark Cox White M
Sale

Gola Men's Tennis Mark Cox White M

$77.00 CAD $110.00 CAD
Gola Men's Harrier Leather White M
Gola Men's Harrier Leather White M
Gola Men's Harrier Leather White M
Gola Men's Harrier Leather White M
Sale

Gola Men's Harrier Leather White M

$112.00 CAD $160.00 CAD
Gola Men's Harrier Leather White/Green/Green M
Gola Men's Harrier Leather White/Green/Green M
Gola Men's Harrier Leather White/Green/Green M
Sale

Gola Men's Harrier Leather White/Green/Green M

$112.00 CAD $160.00 CAD
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Gola Men's Torpedo Leather White M
Sale

Gola Men's Torpedo Leather White M

$122.50 CAD $175.00 CAD

Shop all the brands you love, in one place:

Flats
Women's Sneakers
Women's Sneakers
Men's Casual Shoes
Men's Casual Shoes
Women's Heels
Heels

WIDE FIT BOOTS

SHOP NOW

ANKLE BOOTS

SHOP NOW

KNEE HIGH BOOTS

SHOP NOW

BROWN BOOTS

SHOP NOW

FOR THE LOVE OF SHOES

WE'RE GRATEFUL FOR THE CONTINUED SUPPORT OF OUR SMALL CANADIAN BUSINESS FOR THE LAST 26+ YEARS!

- TEAM HEEL BOY

info@heelboy.com

Office Edit
Kitten Heels
Cowboy Boots
Mary Jane Flats

CURRENT BEST SELLERS

For a reason, discover why for yourself

Shop Now
Ry & Ginger Women's Soho in Black
Ry & Ginger Women's Soho in Black
Ry & Ginger Women's Soho in Black
✨Bestseller✨

Ry & Ginger Women's Soho in Black

$250.00 CAD
Vagabond Women's 5002 Hedda in Black
✨Bestseller✨

Vagabond Women's 5002 Hedda in Black

$260.00 CAD
G.H. Bass Women's Whitney Super Lug Weejun in Black
G.H. Bass Women's Whitney Super Lug Weejun in Black
G.H. Bass Women's Whitney Super Lug Weejun in Black
G.H. Bass Women's Whitney Super Lug Weejun in Black
G.H. Bass Women's Whitney Super Lug Weejun in Black
✨Bestseller✨

G.H. Bass Women's Whitney Super Lug Weejun in Black

$285.00 CAD
 
 ✨Bestseller✨

G.H. Bass Women's Whitney Weejun in Black

$270.00 CAD
Jeffrey Campbell Women's Dancerina Dark Beige/Pu M
Jeffrey Campbell Women's Dancerina Dark Beige/Pu M
Trending Balletcore

Jeffrey Campbell Women's Dancerina Dark Beige/Pu M

$148.00 CAD $185.00 CAD
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
✨Bestseller✨

UGG Women's Classic ll Mini Boot in Chestnut

$190.00 CAD
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
UGG Women's Classic Ultra Mini in Chestnut
✨Bestseller✨

UGG Women's Classic Ultra Mini in Chestnut

$185.00 CAD
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
Badgley Mischka Women's Sacred in Blue
✨Bestseller✨

Badgley Mischka Women's Sacred in Blue

$350.00 CAD
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
Badgley Mischka Women's Sacred in Blush
✨Bestseller✨

Badgley Mischka Women's Sacred in Blush

$350.00 CAD
Badgley Mischka Women's Sacred in White
Badgley Mischka Women's Sacred in White
Badgley Mischka Women's Sacred in White
✨Bestseller✨

Badgley Mischka Women's Sacred in White

$350.00 CAD
Badgley Mischka Women's Libby in White
Badgley Mischka Women's Libby in White
Badgley Mischka Women's Libby in White
Badgley Mischka Women's Libby in White
✨Bestseller✨

Badgley Mischka Women's Libby in White

$350.00 CAD
Kennie Rylie Women's Pirouette in Silver
Kennie Rylie Women's Pirouette in Silver
Kennie Rylie Women's Pirouette in Silver
Kennie Rylie Women's Pirouette in Silver
Kennie Rylie Women's Pirouette in Silver
✨Bestseller✨

Kennie Rylie Women's Pirouette in Silver

$100.00 CAD
+1
Kennie Rylie Women's Pirouette in Black
Kennie Rylie Women's Pirouette in Black
Kennie Rylie Women's Pirouette in Black
Kennie Rylie Women's Pirouette in Black
Kennie Rylie Women's Pirouette in Black
✨Bestseller✨

Kennie Rylie Women's Pirouette in Black

$100.00 CAD
+1
Kennie Rylie Women's Pirouette in Red
Kennie Rylie Women's Pirouette in Red
Kennie Rylie Women's Pirouette in Red
Kennie Rylie Women's Pirouette in Red
Kennie Rylie Women's Pirouette in Red
✨Bestseller✨

Kennie Rylie Women's Pirouette in Red

$100.00 CAD
+1
Alohas Women's Luke in Wine
✨Bestseller✨

Alohas Women's Luke in Wine

$325.00 CAD
Ilse Jacobsen Women's Tulip in Atmosphere
Ilse Jacobsen Women's Tulip in Atmosphere
✨Bestseller✨

Ilse Jacobsen Women's Tulip in Atmosphere

$55.00 CAD $110.00 CAD
+4
Ilse Jacobsen Women's Tulip in Kit
✨Bestseller✨

Ilse Jacobsen Women's Tulip in Kit

$55.00 CAD $110.00 CAD
+4
Ilse Jacobsen Women's Tulip Platform in Black
✨Bestseller✨

Ilse Jacobsen Women's Tulip Platform in Black

$115.00 CAD
Ilse Jacobsen Women's Tulip Platform in White
Ilse Jacobsen Women's Tulip Platform in White
Ilse Jacobsen Women's Tulip Platform in White
Ilse Jacobsen Women's Tulip Platform in White
Ilse Jacobsen Women's Tulip Platform in White
✨Bestseller✨

Ilse Jacobsen Women's Tulip Platform in White

$115.00 CAD
UGG Women's Classic Mini Platform in Chestnut
UGG Women's Classic Mini Platform in Chestnut
UGG Women's Classic Mini Platform in Chestnut
✨Bestseller✨

UGG Women's Classic Mini Platform in Chestnut

$144.45 CAD

AS SEEN ON TIK TOK

UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
UGG Women's Classic ll Mini Boot in Chestnut
✨Bestseller✨

UGG Women's Classic ll Mini Boot in Chestnut

$190.00 CAD
Ugg Women's Tasman Maxi Curly in Chestnut

Ugg Women's Tasman Maxi Curly in Chestnut

$165.00 CAD
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural
Ugg Women's Tasman Maxi Curly in Natural

Ugg Women's Tasman Maxi Curly in Natural

$165.00 CAD
UGG Women's Classic Ultra Mini in Sand
UGG Women's Classic Ultra Mini in Sand
UGG Women's Classic Ultra Mini in Sand
UGG Women's Classic Ultra Mini in Sand
UGG Women's Classic Ultra Mini in Sand
UGG Women's Classic Ultra Mini in Sand
Sale

UGG Women's Classic Ultra Mini in Sand

$157.20 CAD $185.00 CAD