Skip to main content
The Simons members:
free shipping over $50 and free returns (exceptions may apply)

All Our Men's Shoes

FEATURED


Aldair Chelsea boots
Men
discounted price Can$150.00
Steve Madden
Aldair Chelsea boots
Men
discounted price Can$150.00
Steve Madden

New

Leather lace-up boots
Men
discounted price Can$295.00
Simons
Decanto lace-up boots
Men
discounted price Can$220.00
Steve Madden

New

Leather lace-up boots
Men
discounted price Can$295.00
Simons
Decanto lace-up boots
Men
discounted price Can$220.00
Steve Madden
Thorton zipped boots
Men
discounted price Can$349.00
HUGO
Owen glossy leather Chelsea boots
Men
discounted price Can$298.00
Polo Ralph Lauren

Gift Card

Sometimes, the best present is letting them pick.

Boots

New

Leather lace-up boots
Men
discounted price Can$295.00
Simons

New

Leather lace-up boots
Men
discounted price Can$295.00
Simons

New

Leather Chelsea boots
Men
discounted price Can$295.00
Simons
Leather Western boots
Men
discounted price Can$425.00
Simons

New

Tabi Santori Chelsea boots
Men
discounted price Can$285.00
Steve Madden
Decanto lace-up boots
Men
discounted price Can$220.00
Steve Madden
Decanto lace-up boots
Men
discounted price Can$220.00
Steve Madden
Aldair Chelsea boots
Men
discounted price Can$150.00
Steve Madden
Aldair Chelsea boots
Men
discounted price Can$150.00
Steve Madden
Stergis Western boots
Men
discounted price Can$325.00
Steve Madden
Grained leather Ranger boots discounted price Can$298.00
Polo Ralph Lauren
Owen glossy leather Chelsea boots
Men
discounted price Can$298.00
Polo Ralph Lauren
Owen glossy leather Chelsea boots
Men
discounted price Can$298.00
Polo Ralph Lauren
Thorton zipped boots
Men
discounted price Can$349.00
HUGO

New

Faux-fur Chelsea 2976 boots
Men
discounted price Can$250.00
Dr. Martens

New

1460 Pascal faux-fur boots
Men
discounted price Can$250.00
Dr. Martens

New

Euro Hiker hiking boots
Men
discounted price Can$210.00
Timberland
Classic 2544 Chelsea boots
Men
discounted price Can$275.00
Blundstone
1308 Chelsea boots
Men
discounted price Can$260.00
Blundstone
558 Chelsea boots
Men
discounted price Can$250.00
Blundstone
2429 nubuck leather boots
Men
discounted price Can$280.00
Blundstone
584 Chelsea boots
Men
discounted price Can$300.00
Blundstone
Barmoor brogue boots
Men
discounted price Can$355.00
Barbour

New

Fero 2.0 black winter boot
Men
discounted price Can$225.00
Pajar Canada

New

Yargen coffee winter boots
Men
discounted price Can$250.00
Pajar Canada

New

Highwood Mid waterproof lace-up boots
Men
discounted price Can$300.00
Birkenstock

New

Highwood Chelsea boots
Men
discounted price Can$260.00
Birkenstock

New

Dry rubber boots
Men
discounted price Can$200.00
Rains
Base Camp 100 waterproof boots
Men
discounted price Can$240.00
The North Face

New

Glenclyffe waterproof insulated boots
Men
discounted price Can$210.00
The North Face
M120 Alto hiking boots
Men
discounted price Can$725.00
Simons x Fracap
Toscano Volanto M140 hiking boots
Men
discounted price Can$750.00
Simons x Fracap
M121 Commando hiking shoes
Men
discounted price Can$650.00
Simons x Fracap
Suede loafer boots
Unisex
discounted price Can$450.00
JW Anderson x UGG
Suede loafer boots
Unisex
discounted price Can$450.00
JW Anderson x UGG
Suede loafer boots
Unisex
discounted price Can$450.00
JW Anderson x UGG
Winter sole discounted price Can$10.00
Walter's

Sneakers

BadBo 1.1 sneakers
Bad Bunny x adidas
Men
discounted price Can$160.00
Adidas Originals
Samba OG snakeskin sneakers
Men
discounted price Can$160.00
Adidas Originals
Crackled detail Samba OG sneakers
Men
regular price $130.00 discounted price Can$99.95
Adidas Originals
Adimule cowhide pony hair leather mules
Men
regular price $140.00 discounted price Can$99.95
Adidas Originals
Samba OG chestnut sneakers
Men
discounted price Can$130.00
Adidas Originals

New

Gazelle Indoor bronze sneakers
Men
discounted price Can$160.00
Adidas Originals
BW Army brown sneakers
Men
discounted price Can$160.00
Adidas Originals
Green Handball Spezial mixed media sneakers
Men
regular price $140.00 discounted price Can$99.95
Adidas Originals
Samba OG sneakers
Men
discounted price Can$130.00
Adidas Originals
Samba OG sneakers
Men
discounted price Can$130.00
Adidas Originals
Handball Spezial crackled leather sneakers
Men
regular price $140.00 discounted price Can$99.95
Adidas Originals
BW Army sneakers
Men
discounted price Can$160.00
Adidas Originals
Adistar XLG 2.0 sneakers
Men
regular price $180.00 discounted price Can$99.95
Adidas Originals

New

Moon Shoe OG sneakers
Men
discounted price Can$135.00
Nike

Editor's pick

Air Force 1 '07 sneakers
Men
discounted price Can$150.00
Nike

Editor's pick

Air Force 1 '07 sneakers
Men
discounted price Can$150.00
Nike

Men's Shoes

Men's shoes are not just a functional necessity but a statement of style and personality. At Simons, we offer a diverse range of men's footwear that caters to various tastes and occasions. From classic leather dress shoes that exude sophistication to casual sneakers for a laid-back vibe, our collection ensures there's a perfect pair for every man. Whether you're stepping into the office, hitting the gym, or simply going about your day, your choice of shoes can greatly impact your overall look and comfort. Our selection includes a variety of designs, materials, and colours, allowing you to express your individual style and complement any outfit. Whether you prefer the timeless elegance of brogues, the rugged versatility of boots, or the athletic comfort of trainers, Simons' men's shoes provide the perfect blend of fashion and function. Elevate your footwear game with our range of shoes and make a lasting impression wherever you go.