Men's Dress Shoes on Sale – heel boy

Skip to content

Kingston Store
Toronto Store
Gift Cards

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

Country/region

Facebook
Instagram
TikTok

Search

Most searched products

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

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

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

Regular price €169,95 EUR

Sale price €169,95 EUR Regular price

Unit price

/per

Choose your option

Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

Regular price €163,95 EUR

Sale price €163,95 EUR Regular price

Unit price

/per

Choose your option

Kennie Rylie Women's Pirouette in Red

Kennie Rylie Women's Pirouette in Red

Kennie Rylie Women's Pirouette in Red

Regular price €62,95 EUR

Sale price €62,95 EUR Regular price

Unit price

/per

Choose your option

UGG Women's Classic Micro in Sand

UGG Women's Classic Micro in Sand

UGG Women's Classic Micro in Sand

Regular price €109,95 EUR

Sale price €109,95 EUR Regular price

Unit price

/per

Choose your option

FLOOF Women's Plush Blanket Scarf in Blue Multi

FLOOF Women's Plush Blanket Scarf in Blue Multi

Regular price €37,95 EUR

Sale price €37,95 EUR Regular price

Unit price

/per

Choose your option

New Balance Women's 327 in Sea Salt

New Balance Women's 327 in Sea Salt

New Balance Women's 327 in Sea Salt

Regular price €81,95 EUR

Sale price €81,95 EUR Regular price

Unit price

/per

Choose your option

Most searched keywords

UGG
PAJAR
CAMPER
Aquatalia
Badgley Mischka
Hunter
New Balance 327
Tall Boots
Women's Winter Boots
Vagabond

Our Canada Stores Sign in/ Register Cart

Women
Shop by Type

Sneakers

Boots

Heels

Flats

Sandals

Slippers

All Gendered

Shop All Women's Shoes

Shop by Occasion

Holiday Party

Rain

Snow & Winter

Office & Workwear

Gift Guides

Weddings & Events

Vacation & Resort

Shop All Women's Shoes

Shop by Trend

Bestsellers

New Arrivals

Bows

Polka Dots

Holiday Hues

Animal Print

Shop All Women's Shoes

Shop by Brand

Badgley Mischka

Camper

G.H. Bass

Hanky Panky

La Canadienne

Miz Mooz

New Balance

Sam Edelman

UGG

Vagabond Shoemakers

Shop All Brands

Accessories

Shop All Accessories

Jackets & Coats

Handbags & Totes

Scarves & Hats

Socks & Intimates

Sunglasses

Mittens & Gloves

Travel Accessories

Umbrellas

Shoe Care

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

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

Shoe Care

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
Merrell Kids'
Saucony Kids'

All Kids' Shoes

Kids' Winter Boots

Kids' Rain Boots
Accessories

Bags
Hats & Scarves
Socks & Intimates
Shoe Care
Shop All Accessories

Mittens & Gloves
Jackets & Coats
Sunglasses
Umbrellas

Seasonal Favourites

FLOOF Women's Plush Blanket Scarf in Red
Regular price €37,95 EUR

Sale price €37,95 EUR Regular price

Unit price
per

View details

Rains Hilo Weekend Bag in Spill
Regular price €87,95 EUR

Sale price €87,95 EUR Regular price

Unit price
per

View details

Hestra Men's Basic Wool Glove in Charcoal
Regular price €47,95 EUR

Sale price €47,95 EUR Regular price

Unit price
per

View details

FLOOF Women's Wool Hat in Dark Green, O/S
Regular price €25,95 EUR

Sale price €25,95 EUR Regular price

Unit price
per

View details

Rains Alta Puffer Mittens in Navy
Regular price €64,95 EUR

Sale price €64,95 EUR Regular price

Unit price
per

View details

Floof 2 Pack Cable Knit Socks in Beige and Cream
Regular price €11,95 EUR

Sale price €11,95 EUR Regular price

Unit price
per

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

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

C
Calvin Klein
Camper
Clarks
Cobb Hill
Cole Haan
Colmar
Cougar
I
Ilse Jacobsen
Intentionally Blank
Ipanema
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
Jambu
JBU
Jeffrey Campbell
Jessica Simpson
Jewel by Badgley Mischka
Johnston & Murphy
R
RAINS
Reebok
Reebok Apparel
Reef
Rebecca Minkoff
Religious Comfort
Rockport
Ry & Ginger

E
Earth
Easy Spirit
ECCO
K
Kenneth Cole
Kenneth Cole Men
Kenneth Cole Reaction
Kennie Rylie
S
Sam Edelman
SANDQVIST
Santana Canada
Saucony
Saucony Kids'
Sister X Soeur
Sorel
Sperry
Steve Madden

F
FitFlop
FLOOF
Free People
Frye
FUBUKI
L
La Boucle
La Canadienne
Lemon Jelly
Lucky Brand
Lyla & Luxe
T
Teva
TKEES
Tommy Hilfiger
Tretorn
Deals
Shop by brand

Nine West 30% OFF

MoEa 50% OFF

Ilse Jacbosen 50% OFF

Allbirds 50% OFF

Vince Camuto 20% OFF

Shop All Sale

All Sale

Men's Sale Styles

Women' Sale Styles

Shop All Sale
About
Blog

Women
- Shop by Type
  
  Sneakers
  
  Boots
  
  Heels
  
  Flats
  
  Sandals
  
  Slippers
  
  All Gendered
  
  Shop All Women's Shoes
- Shop by Occasion
  
  Holiday Party
  
  Rain
  
  Snow & Winter
  
  Office & Workwear
  
  Gift Guides
  
  Weddings & Events
  
  Vacation & Resort
  
  Shop All Women's Shoes
- Shop by Trend
  
  Bestsellers
  
  New Arrivals
  
  Bows
  
  Polka Dots
  
  Holiday Hues
  
  Animal Print
  
  Shop All Women's Shoes
- Shop by Brand
  
  Badgley Mischka
  
  Camper
  
  G.H. Bass
  
  Hanky Panky
  
  La Canadienne
  
  Miz Mooz
  
  New Balance
  
  Sam Edelman
  
  UGG
  
  Vagabond Shoemakers
  
  Shop All Brands
- Accessories
  
  Shop All Accessories
  
  Jackets & Coats
  
  Handbags & Totes
  
  Scarves & Hats
  
  Socks & Intimates
  
  Sunglasses
  
  Mittens & Gloves
  
  Travel Accessories
  
  Umbrellas
  
  Shoe Care
- 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
  
  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
  
  Shoe Care
  
  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
  Merrell Kids'
  Saucony Kids'
Accessories
- Bags
- Mittens & Gloves
- Hats & Scarves
- Jackets & Coats
- Socks & Intimates
- Sunglasses
- Shoe Care
- Umbrellas
- Shop All Accessories
Shop By Brand
Deals
- Shop by brand
  
  Nine West 30% OFF
  
  MoEa 50% OFF
  
  Ilse Jacbosen 50% OFF
  
  Allbirds 50% OFF
  
  Vince Camuto 20% OFF
  
  Shop All Sale
- All Sale
  
  Men's Sale Styles
  
  Women' Sale Styles
  
  Shop All Sale
About
Blog

Our Canada Stores Sign in/ Register

Country/region

Facebook
Instagram
TikTok

Home Collection Men's Dress Shoes on Sale

Styles & sizes will vary online and in stores.

Collection: Men's Dress Shoes on Sale

Shop men’s shoes, boots, and sneakers—crafted for comfort, now on sale.

All Sale

All Sale

Under $100

Under $100

Boots

Boots

Casual Shoes

Casual Shoes

Dress Shoes

Dress Shoes

Sneakers

Sneakers

Sandals

Sandals

Slippers

Slippers

Compare (0/5)

9 products

Filter

Sort by:

Brand

COLE HAAN 3
STEVE MADDEN 6

Colour

Beige 1
Black 4
Brown 4

Material

Leather 1

Shoe features

Waterproof 8

Product type

Men's Dress Shoes 9

Size

8 5
8.5 2
9 1
9.5 3
10 3
11 6
12 2
13 1

Compare:

Sort by:

View as:

Brand

COLE HAAN 3
STEVE MADDEN 6

Colour

Beige 1
Black 4
Brown 4

Material

Leather 1

Shoe features

Waterproof 8

Product type

Men's Dress Shoes 9

Size

8 5
8.5 2
9 1
9.5 3
10 3
11 6
12 2
13 1

Cole Haan Men's American Classics Penny Loafer in Sesame/Egret

Compare

Cole Haan Men's American Classics Penny Loafer in Sesame/Egret

Regular price €75,95 EUR

Sale price €75,95 EUR Regular price

Unit price

/per

Choose your option

Cole Haan Men's Modern Essentials Plain Toe Oxford in Black

Compare

Cole Haan Men's Modern Essentials Plain Toe Oxford in Black

Regular price From €158,95 EUR

Sale price From €158,95 EUR Regular price

Unit price

/per

Choose your option

Cole Haan Men's Modern Essentials Wing Oxford in Black

Cole Haan Men's Modern Essentials Wing Oxford in Black

Compare

Cole Haan Men's Modern Essentials Wing Oxford in Black

Regular price €144,95 EUR

Sale price €144,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Daegan in Black

Steve Madden Men's Daegan in Black

Compare

Steve Madden Men's Daegan in Black

Regular price From €79,95 EUR

Sale price From €79,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Daegan in Brown

Steve Madden Men's Daegan in Brown

Compare

Steve Madden Men's Daegan in Brown

Regular price From €79,95 EUR

Sale price From €79,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Efrian in Brown

Steve Madden Men's Efrian in Brown

Compare

Steve Madden Men's Efrian in Brown

Regular price €67,95 EUR

Sale price €67,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Emmeric in Black

Steve Madden Men's Emmeric in Black

Compare

Steve Madden Men's Emmeric in Black

Regular price €79,95 EUR

Sale price €79,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Emmeric in Brown

Steve Madden Men's Emmeric in Brown

Compare

Steve Madden Men's Emmeric in Brown

Regular price €79,95 EUR

Sale price €79,95 EUR Regular price

Unit price

/per

Choose your option

Steve Madden Men's Jarring in Brown

Steve Madden Men's Jarring in Brown

Compare

Steve Madden Men's Jarring in Brown

Regular price €64,95 EUR

Sale price €64,95 EUR Regular price

Unit price

/per

Choose your option

Men's Dress Shoes on Sale

Invest in your wardrobe for less. These Men's Dress Shoes on sale offers quality, premium leather, and essential styles at a smart discount.

heel boy

Women's Sale

heel boy

Men's Sale

Fast Delivery

14 Days Free Returns

Secure Payment

Worldwide Shipping

Proudly Canadian

Recently viewed products

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

Customer Service

Mon-Fri, 9am-5pm EST.

Call Us

+1 (416) 367-4335

Get in Touch

info@heelboy.com

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

© 2025 heel boy. Powered by Shopify

✌🏼 Free Express Shipping on orders $150!

Your cart

Your cart is currently empty.

Not sure where to start? Try these collections:

Women's New Arrivals
Men's New Arrivals
Bestsellers
Women's Flats
Women's Snow Ready Styles
Men's Snow Ready Styles
All Accessories
Men's Casual Shoes

Continue shopping

You are eligible for free shipping. Spend €0,00 more to reach free shipping!

Order note

Order note

Estimate Shipping

Country/region

Province

Postal/ZIP code

Coupon

Coupon

Estimated total €0,00 EUR

Taxes and shipping calculated at checkout

View cart

Product Comparison

Description

Price

Vendor

Type

Product variants

It's now or never for these deals | All sales final

Currently on sale (6)

Ilse Jacobsen 50% OFF

The Tulip Flat

SHOP NOW

MoEa 50% off

Prices as marked

SHOP NOW

Allbirds 50% OFF

Prices as marked

SHOP NOW

Vince Camuto 40% Off

Select Styles

SHOP NOW

Diesel 40% OFF

Prices as marked

SHOP NOW

Marc Fisher 20% Off

Select Styles

SHOP NOW

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