Men's New Arrivals Fall Shoes – Page 16 – heel boy

Skip to content

Kingston Store
Toronto Store
Gift Cards

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

Language

English
Français

Country/region

Facebook
Instagram
TikTok

⚡ END OF SUMMER FLASH: UP TO 70% OFF | PRICES AS MARKED

Search

Most searched products

Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

Regular price $260.00 CAD

Sale price $260.00 CAD Regular price

Unit price

/per

Choose your option

black leather block heel pump with bow detail on a white background

heel boy Women's Paloma in Black

heel boy Women's Paloma in Black

Regular price $200.00 CAD

Sale price $200.00 CAD Regular price

Unit price

/per

Choose your option

brown ballet flats on a white background

Camper Women's Casi Myra K201253-057 in Brown

NEW

Camper Women's Casi Myra K201253-057 in Brown

Regular price $205.00 CAD

Sale price $205.00 CAD Regular price

Unit price

/per

Choose your option

Pair of checkered gingham socks with black ruffle details on a white background

FLOOF Gingham Frill Sock in Black and White

Regular price $12.00 CAD

Sale price $12.00 CAD Regular price

Unit price

/per

Choose your option

Sam Edelman Women's Magnolia in Java Brown

Sam Edelman Women's Magnolia in Java Brown

Sam Edelman Women's Magnolia in Java Brown

Regular price $156.00 CAD

Sale price $156.00 CAD Regular price

Unit price

/per

Choose your option

cognac brown suede penny loafer on a white background

Miz Mooz Women's Vayda in Cognac

Miz Mooz Women's Vayda in Cognac

Regular price $190.00 CAD

Sale price $190.00 CAD Regular price

Unit price

/per

Choose your option

Embroidered black hat with "Spooky Season" on a white background

Floof Unisex Spooky Season Cap in Black

Regular price $40.00 CAD

Sale price $40.00 CAD Regular price

Unit price

/per

Choose your option

olive and beige houndstooth fabric sneaker on a white background

Back 70 Women's Cloud UK04 in Loden Olive/Olive

NEW

Back 70 Women's Cloud UK04 in Loden Olive/Olive

Regular price $220.00 CAD

Sale price $220.00 CAD Regular price

Unit price

/per

Choose your option

Most searched keywords

CAMPER CASIMYRA
SAM EDELMAN ALIE
FRYE BOOTS
ARCHIES FLIP FLIOP
BROWN SUEDE
LOAFERS
NEW BALANCE

Our Canada Stores Sign in/ Register Cart

Women
Shop by Type

Boots

Flats

Heels

Sandals

Sneakers

Slippers

Winter Boots

All Gendered

Shop All Women's Shoes

Shop by Occasion

Back to School

Rain

Weddings & Events

Gardening

Hiking Sandals

Office & Workwear

Vacation & Resort

Snow & Winter

Shop All Women's Shoes

Shop by Trend

Bestsellers

Spring New Arrivals

Currently Loving

Jelly Flats & Sandals

Mesh Footwear

Woven Detail

Sneaker Mules

Sneakerinas

Slogan Hats

Shop All Women's Shoes

Shop by Brand

Badgley Mischka

Camper

G.H. Bass

Hanky Panky

Miz Mooz

New Balance

Sam Edelman

UGG

Vagabond Shoemakers

Shop All Brands

Accessories

Jackets & Coats

All Bags

Baseball Hats

Clutches

Hair Accessories

Socks & Intimates

Sunglasses

Umbrellas

Mittens & Gloves

Scarves & Hats

Travel Accessories

Shop All Accessories

Shop by Feature

Arch Support

Extended Width

Lightweight

Removable Insole

Podiatrist Recommended

Recycled Materials

Slip Resistant

Waterproof

Vegan

Shop All Women's Shoes

Shop by Weather

Rain Ready

Snow Ready

Ice Gripper Outsole

Weatherproof Leather

Weatherproof Suede

Deals

Under $100

Shop All Sale
Men
Shop by Type

Sneakers

Boots

Loafers

Dress Shoes

Sandals

Chukka Boots

Oxford Shoes

Slippers

All Gendered

Shop All Men's Shoes

Shop by Occasion

Events & Weddings

Work Boots

Running Shoes

Snow & Winter

Hiking

Gift Guide

House Shoes

Father's Day Shop

Shop All Men's Shoes

Shop by Trend

Bestsellers

New In

Combat Boots

Shop All Men's Shoes

Shop by Brand

Cole Haan

G.H. Bass

Johnston & Murphy

New Balance

On Running

Palladium

Pajar

Xtratuf

Shop All Brands

Accessories

Belts

Umbrellas

Travel Bags & Accessories

Mittens & Gloves

Socks & Boxers

Jackets & Coats

Hats & Scarves

Groom Care

Shop All Accessories

Shop by Feature

Cushioned Shoes

Breathable Upper

Extended Width

Removable Insole

Lightweight Shoes

Slip Resistant

Steel Toe

Waterproof

Vegan

Shop All Men's Shoes

Shop by Weather

Rain Ready

Snow Ready

Weatherproof Leather

Weatherproof Suede

Ice Gripper Outsole

Deals

Under $100

Shop All Men's Sale
Kids'
Shop by Type
New Arrivals
Boots
Flats
Rain Boots
Sneakers
Sandals
Winter Boots
Shop All

Shop by Brand
Badgley Mishcka Kids
Cougar Kids
Camper Kids
Joybees Kids
Merrell Kids'
Saucony Kids'

All Kids' Shoes

Kids' Winter Boots

Kids' Rain Boots
Accessories

Bags
Hats & Scarves
Socks & Intimates
Sunglasses
Umbrellas

Mittens & Gloves
Jackets & Coats
Hair Accessories
Shoe Care
Shop All Accessories

Seasonal Favourites

Floof Gingham Frill Sock in Navy
Regular price $12.00 CAD

Sale price $12.00 CAD Regular price

Unit price
per

View details

Kennie Rylie Retro Aviator Sunnies in Black/Blue
Regular price $30.00 CAD

Sale price $30.00 CAD Regular price

Unit price
per

View details

heel boy Women's Half Moon Claw Clip in Cherry Red
Regular price $14.00 CAD

Sale price $14.00 CAD Regular price

Unit price
per

View details
Shop By Brand
A
Allbirds
Alohas
American Glamour
Angel Alarcon
Archies
Aquatalia
Aquatherm Canada
Astorflex
Ateliers
G
Gentle Souls by Kenneth Cole
Georgia Boots
G.H. BASS
Gola
Goorin Bros®
GRAHAME JAMES
GROOM
M
Made For The People
Marc Fisher LTD
Melissa
Merrell Kids'
Miz Mooz
MoEa
Mollini
Moses
Muck Boot Company
U
UGG
Uppdoo

B
BACK 70
Badgley Mischka
Badgley Mischka Handbags
Badgley Mischka Kids
Bag & Bougie
Blondo
BN3TH
Børn
Brave Leather
Bueno
H
Hanky Panky
Havaianas
Hestra
Hunter
N
Native Shoes
Naturalizer
New Balance
Nine West
V
Vagabond Shoemakers
Vince.
Vince Camuto
Vionic

C
Calvin Klein
Camper
Cobb Hill
Cole Haan
Cougar
I
Ilse Jacobsen
Intentionally Blank
Italian Shoemakers
O-P
OluKai
On Running
Pajar
Palladium
W-X
Walter's Shoe Care
Wonders
Xtratuf

D
David Tyler
Diesel
Django & Juliette
Dockers
Dolce Vita
Dunham Men
Durango
J
JBU
Jeffrey Campbell
Jewel by Badgley Mischka
Johnston & Murphy
Joybees
Joybees Kids
R
RAINS
Reebok
Reebok Apparel
Reef
Rebecca Minkoff
Religious Comfort
Rocky
Rockport
Ry & Ginger

E
Earth
Easy Spirit
ECCO
K
Keen
Kenneth Cole
Kenneth Cole Men
Kenneth Cole Reaction
Kennie Rylie
S
Sam Edelman
SANDQVIST
Santana Canada
Saucony
Saucony Kids'
Sebago
Sorel
Sperry
Steve Madden
Suicoke
Superga

F
FitFlop
FLOOF
Florsheim
Free People
Frye
Frye & Co
FUBUKI
L
La Boucle
La Canadienne
Lemon Jelly
Lucky Brand
Lyla & Luxe
T
Teva
TKEES
Tommy Hilfiger
Tretorn
two.B MTL
Deals
Shop by type
Boots
Flats
Heels
Sandals
Sneakers
Men's Boots
Men's Sneakers

All Sale
Men's Sale Styles
Women's Sale Styles
Shop All Sale

FINAL SALE

Camper Women's Louise Sandal K201915-002 In White
Regular price $60.00 CAD

Sale price $60.00 CAD Regular price ~~$200.00 CAD~~

Unit price
per

View details

Fitflop Women's Lulu Lux Graphic-Weave Toe-Post in Black
Regular price $136.00 CAD

Sale price $136.00 CAD Regular price ~~$170.00 CAD~~

Unit price
per

View details
About
Blog

Women
- Shop by Type
  
  Boots
  
  Flats
  
  Heels
  
  Sandals
  
  Sneakers
  
  Slippers
  
  Winter Boots
  
  All Gendered
  
  Shop All Women's Shoes
- Shop by Occasion
  
  Back to School
  
  Rain
  
  Weddings & Events
  
  Gardening
  
  Hiking Sandals
  
  Office & Workwear
  
  Vacation & Resort
  
  Snow & Winter
  
  Shop All Women's Shoes
- Shop by Trend
  
  Bestsellers
  
  Spring New Arrivals
  
  Currently Loving
  
  Jelly Flats & Sandals
  
  Mesh Footwear
  
  Woven Detail
  
  Sneaker Mules
  
  Sneakerinas
  
  Slogan Hats
  
  Shop All Women's Shoes
- Shop by Brand
  
  Badgley Mischka
  
  Camper
  
  G.H. Bass
  
  Hanky Panky
  
  Miz Mooz
  
  New Balance
  
  Sam Edelman
  
  UGG
  
  Vagabond Shoemakers
  
  Shop All Brands
- Accessories
  
  Jackets & Coats
  
  All Bags
  
  Baseball Hats
  
  Clutches
  
  Hair Accessories
  
  Socks & Intimates
  
  Sunglasses
  
  Umbrellas
  
  Mittens & Gloves
  
  Scarves & Hats
  
  Travel Accessories
  
  Shop All Accessories
- Shop by Feature
  
  Arch Support
  
  Extended Width
  
  Lightweight
  
  Removable Insole
  
  Podiatrist Recommended
  
  Recycled Materials
  
  Slip Resistant
  
  Waterproof
  
  Vegan
  
  Shop All Women's Shoes
- Shop by Weather
  
  Rain Ready
  
  Snow Ready
  
  Ice Gripper Outsole
  
  Weatherproof Leather
  
  Weatherproof Suede
- Deals
  
  Under $100
  
  Shop All Sale
Men
- Shop by Type
  
  Sneakers
  
  Boots
  
  Loafers
  
  Dress Shoes
  
  Sandals
  
  Chukka Boots
  
  Oxford Shoes
  
  Slippers
  
  All Gendered
  
  Shop All Men's Shoes
- Shop by Occasion
  
  Events & Weddings
  
  Work Boots
  
  Running Shoes
  
  Snow & Winter
  
  Hiking
  
  Gift Guide
  
  House Shoes
  
  Father's Day Shop
  
  Shop All Men's Shoes
- Shop by Trend
  
  Bestsellers
  
  New In
  
  Combat Boots
  
  Shop All Men's Shoes
- Shop by Brand
  
  Cole Haan
  
  G.H. Bass
  
  Johnston & Murphy
  
  New Balance
  
  On Running
  
  Palladium
  
  Pajar
  
  Xtratuf
  
  Shop All Brands
- Accessories
  
  Belts
  
  Umbrellas
  
  Travel Bags & Accessories
  
  Mittens & Gloves
  
  Socks & Boxers
  
  Jackets & Coats
  
  Hats & Scarves
  
  Groom Care
  
  Shop All Accessories
- Shop by Feature
  
  Cushioned Shoes
  
  Breathable Upper
  
  Extended Width
  
  Removable Insole
  
  Lightweight Shoes
  
  Slip Resistant
  
  Steel Toe
  
  Waterproof
  
  Vegan
  
  Shop All Men's Shoes
- Shop by Weather
  
  Rain Ready
  
  Snow Ready
  
  Weatherproof Leather
  
  Weatherproof Suede
  
  Ice Gripper Outsole
- Deals
  
  Under $100
  
  Shop All Men's Sale
Kids'
- Shop by Type
  
  New Arrivals
  Boots
  Flats
  Rain Boots
  Sneakers
  Sandals
  Winter Boots
  Shop All
- Shop by Brand
  
  Badgley Mishcka Kids
  Cougar Kids
  Camper Kids
  Joybees Kids
  Merrell Kids'
  Saucony Kids'
Accessories
- Bags
- Mittens & Gloves
- Hats & Scarves
- Jackets & Coats
- Socks & Intimates
- Hair Accessories
- Sunglasses
- Shoe Care
- Umbrellas
- Shop All Accessories
Shop By Brand
Deals
- Shop by type
  
  Boots
  Flats
  Heels
  Sandals
  Sneakers
  Men's Boots
  Men's Sneakers
- All Sale
  
  Men's Sale Styles
  Women's Sale Styles
  Shop All Sale
About
Blog

Our Canada Stores Sign in/ Register

Country/region

Language

English
Français

Facebook
Instagram
TikTok

Home Collection Men's New Fall Arrivals

Styles & sizes will vary online and in stores.

Collection: Men's New Fall Arrivals

Step into the season with new men’s shoes and boots designed for Fall—crafted with durable materials, modern design, and all-day comfort.

Boots

Boots

Casual

Casual

Loafers

Loafers

Oxfords

Oxfords

Sneakers

Sneakers

Sandals

Sandals

Slippers

Slippers

Winter Boots

Winter Boots

Waterproof

Waterproof

Compare (0/5)

380 products

Filter

Sort by:

Compare:

Sort by:

View as:

Reebok Unisex' Sidewinder 26 Club Id In Black/Digital M

Reebok Unisex' Sidewinder 26 Club Id In Black/Digital M

Compare

Reebok Unisex' Sidewinder 26 Club Id In Black/Digital M

Regular price $120.00 CAD

Sale price $120.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Unisex' Sidewinder 26 Pro Tf In Black/Digital M

Reebok Unisex' Sidewinder 26 Pro Tf In Black/Digital M

Compare

Reebok Unisex' Sidewinder 26 Pro Tf In Black/Digital M

Regular price $170.00 CAD

Sale price $170.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Unisex' Reebok Glide Low In Chalk/Barely M

Reebok Unisex' Reebok Glide Low In Chalk/Barely M

Compare

Reebok Unisex' Reebok Glide Low In Chalk/Barely M

Regular price $100.00 CAD

Sale price $100.00 CAD Regular price

Unit price

/per

Choose your option

Compare

Reebok Men's Id 2-Colour Logo Fleece Crew Sweatshirt In Black REG

Regular price $75.00 CAD

Sale price $75.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Unisex' Sidewinder 26 Club Tf In Neon Cherry M

Reebok Unisex' Sidewinder 26 Club Tf In Neon Cherry M

Compare

Reebok Unisex' Sidewinder 26 Club Tf In Neon Cherry M

Regular price $120.00 CAD

Sale price $120.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Unisex' Reebok Glide Low In Navy/Vector M

Reebok Unisex' Reebok Glide Low In Navy/Vector M

Compare

Reebok Unisex' Reebok Glide Low In Navy/Vector M

Regular price $100.00 CAD

Sale price $100.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Men's Sidewinder Football Crewneck Sweatshirt In Black/Grey REG

Reebok Men's Sidewinder Football Crewneck Sweatshirt In Black/Grey REG

Compare

Reebok Men's Sidewinder Football Crewneck Sweatshirt In Black/Grey REG

Regular price $140.00 CAD

Sale price $140.00 CAD Regular price

Unit price

/per

Choose your option

Reebok Unisex' Floatzig Encore In Black Black M

Reebok Unisex' Floatzig Encore In Black Black M

Compare

Reebok Unisex' Floatzig Encore In Black Black M

Regular price $190.00 CAD

Sale price $190.00 CAD Regular price

Unit price

/per

Choose your option

black leather oxford on a white background

Vagabond Men's Mario 5861-001-20 in Black

Compare

Vagabond Men's Mario 5861-001-20 in Black

Regular price $240.00 CAD

Sale price $240.00 CAD Regular price

Unit price

/per

Choose your option

black leather penny loafer on a white background

Vagabond Men's Alex M 5366-101-20 in Black

Compare

Vagabond Men's Alex M 5366-101-20 in Black

Regular price $260.00 CAD

Sale price $260.00 CAD Regular price

Unit price

/per

Choose your option

dark brown suede penny loafer on a white background

Vagabond Men's Steven 6060-040-31 in Java

Compare

Vagabond Men's Steven 6060-040-31 in Java

Regular price $270.00 CAD

Sale price $270.00 CAD Regular price

Unit price

/per

Choose your option

dark brown suede oxford on a white background

Vagabond Men's Mario 5861-040-31 in Java

Compare

Vagabond Men's Mario 5861-040-31 in Java

Regular price $240.00 CAD

Sale price $240.00 CAD Regular price

Unit price

/per

Choose your option

black leather penny loafer on a white background

Vagabond Men's Steven 6060-001-20 in Black

Compare

Vagabond Men's Steven 6060-001-20 in Black

Regular price $270.00 CAD

Sale price $270.00 CAD Regular price

Unit price

/per

Choose your option

burgundy sneaker on a white background

New Balance Unisex 574 in Mulled Wine/White

Compare

New Balance Unisex 574 in Mulled Wine/White

Regular price $130.00 CAD

Sale price $130.00 CAD Regular price

Unit price

/per

Choose your option

black and white sneaker on a white background

New Balance Unisex 480P in Black/Sea Salt

Compare

New Balance Unisex 480P in Black/Sea Salt

Regular price $130.00 CAD

Sale price $130.00 CAD Regular price

Unit price

/per

Choose your option

black and white sneaker on a white background

New Balance Unisex 574 in Black/White

Compare

New Balance Unisex 574 in Black/White

Regular price $130.00 CAD

Sale price $130.00 CAD Regular price

Unit price

/per

Choose your option

white sneaker on a white background

New Balance Unisex 480P in Linen/Sea Salt

Compare

New Balance Unisex 480P in Linen/Sea Salt

Regular price $130.00 CAD

Sale price $130.00 CAD Regular price

Unit price

/per

Choose your option

New Balance Unisex 740 in Sea Salt/Truffle Salt

New Balance Unisex 740 in Sea Salt/Truffle Salt

-13%

Compare

New Balance Unisex 740 in Sea Salt/Truffle Salt

Regular price $130.49 CAD

Sale price $130.49 CAD Regular price ~~$149.99 CAD~~

Unit price

/per

Choose your option

dark green leather hiking sneaker on a white background

Keen Men's Jasper Zionic in Dark Olive/Golden Cypress

Compare

Keen Men's Jasper Zionic in Dark Olive/Golden Cypress

Regular price $200.00 CAD

Sale price $200.00 CAD Regular price

Unit price

/per

Choose your option

Franco Sarto Salino in Navy

Franco Sarto Salino in Navy

Compare

Franco Sarto Salino in Navy

Regular price $215.00 CAD

Sale price $215.00 CAD Regular price

Unit price

/per

Choose your option

Prev
1
…
14
15
16
17
18
19
Next

Men's New Fall Arrivals

Fast Delivery

14 Days Returns

Secure Payment

Worldwide Shipping

Proudly Canadian

Recently viewed products

Customer Service

Mon-Fri, 9am-5pm EST.

Call Us

+1 (416) 367-4335

Get in Touch

info@heelboy.com

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

Join Our Newsletter

Sign up to our newsletter & receive 10% off your first order.

Email

You have already subscribed!

By subscribing you agree to the Terms of Services and Privacy Policy.

Help

Contact Us
Shipping & Delivery
Returns Information
Return Portal
FAQs

Shop

Women
Men
Kids'
All Gendered
Accessories
Sale
Gift Cards
Shop All Brands

Account

Our Story
Our Mobile App
Canada Stores
Careers
Blog

Country/region

Payment methods

Facebook
Instagram
TikTok

© 2026 heel boy.

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

Your cart

Your cart is currently empty.

Not sure where to start? Try these collections:

Women's Fall Preview
Men's New Fall Arrivals
Bestsellers
Women's Flats
Women's Sneakers
Women's Boots

Continue shopping

Estimated total $0.00 CAD

Taxes and shipping calculated at checkout

View cart

Product Comparison

Description

Price

Vendor

Type

Product variants

Choosing a selection results in a full page refresh.
Opens in a new window.