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

Boots

Le 31

Featured

Editor's pick

Back-to-Berkeley IV leather waterproof boots
Men discounted price Can$210.00
The North Face

Editor's pick

Back-to-Berkeley IV leather waterproof boots
Men discounted price Can$210.00
The North Face
GreenStride™ Motion 6 winter ankle boots
Men discounted price Can$180.00
Timberland
GreenStride™ Originals Ultra waterproof boots
Men discounted price Can$190.00
Timberland
Boury utilitarian boots
Men discounted price Can$195.00
Dr. Martens
M120 Alto Moro heritage boots
Men discounted price Can$550.00
Simons x Fracap
Stellan lined lace-up boots
Men regular price $260.00 discounted price Can$199.95
Shoe The Bear
585 Chelsea boots
Men discounted price Can$250.00
Blundstone
Urian quilted boots
Men regular price $248.00 discounted price Can$179.95
HUGO

Arbor Road laced boots
Men discounted price Can$220.00
Timberland
Premium 6-inch waterproof lined boots
Men regular price $210.00 discounted price Can$167.95
Timberland
Premium 6-inch waterproof boots
Men discounted price Can$200.00
Timberland
Originals Ultra waterproof lace-up boots
Men discounted price Can$180.00
Timberland
Treeline waterproof lined boots
Men discounted price Can$170.00
Timberland
GreenStride™ Motion 6 winter ankle boots
Men discounted price Can$180.00
Timberland
GreenStride™ Originals Ultra waterproof boots
Men discounted price Can$190.00
Timberland
GreenStride™ Originals Ultra waterproof boots
Men discounted price Can$190.00
Timberland

New

Highland Hi Heritage boots
Men discounted price Can$150.00
UGG
Neumel Chelsea boots
Men discounted price Can$175.00
UGG
Neumel chukka boots
Men discounted price Can$175.00
UGG
Classic Mini boots
Men discounted price Can$200.00
UGG
UGGguard rubber overshoes
Men discounted price Can$65.00
UGG
Neumel Weather Hybrid chukka boots
Men discounted price Can$225.00
UGG
UGGguard rubber overshoes
Men discounted price Can$65.00
UGG
1964 Pac™ nylon winter boots
Men discounted price Can$170.00
Sorel
1964 Pac™ nylon winter boots
Men discounted price Can$170.00
Sorel
Caribou™ winter boots
Men discounted price Can$230.00
Sorel
Caribou™ winter boots
Men discounted price Can$230.00
Sorel
Carson™ Storm waterproof lace-up boots
Men discounted price Can$200.00
Sorel
Forest green Garpa Chelsea rain boots
Men regular price $200.00 discounted price Can$149.95
Tretorn
Garpa Chelsea rain boots
Men regular price $200.00 discounted price Can$149.95
Tretorn
Cold Bay waterproof Chelsea boots
Men regular price $130.00 discounted price Can$99.95
Sperry Top Sider
Cold Bay grey waterproof Chelsea boots
Men regular price $130.00 discounted price Can$99.95
Sperry Top Sider
Black M121 heritage shoes
Men regular price $495.00 discounted price Can$249.95
Simons x Fracap
Explorer R300 heritage boots
Men discounted price Can$525.00
Simons x Fracap
Bordeaux M121 heritage shoes
Men regular price $495.00 discounted price Can$249.95
Simons x Fracap
584 Chelsea boots
Men discounted price Can$290.00
Blundstone
2029 Chelsea boots
Men discounted price Can$265.00
Blundstone
558 Chelsea boots
Men discounted price Can$250.00
Blundstone
1308 Chelsea boots
Men discounted price Can$250.00
Blundstone
Western harness-strap dress boots
Men discounted price Can$225.00
Simons
1118 Western boots
Men discounted price Can$325.00
Simons x Boulet
1118 Western boots
Men discounted price Can$325.00
Simons x Boulet
Cognac Austin western boots
Men discounted price Can$548.00
Frye
Online only
Alex M leather lace-up boots
Men discounted price Can$270.00
Vagabond Shoemakers
Harvey Chelsea ankle boots
Men regular price $265.00 discounted price Can$199.95
Vagabond Shoemakers
Portman dressy Chelsea boots
Men regular price $140.00 discounted price Can$99.95
Steve Madden
Portman dressy Chelsea boots
Men regular price $140.00 discounted price Can$99.95
Steve Madden
Daylon dress boots
Men discounted price Can$210.00
Steve Madden
Daylon dress boots
Men discounted price Can$210.00
Steve Madden
Bowery lace-up boots
Men discounted price Can$548.00
Frye
Online only
1460 Smooth lace-up boots
Men discounted price Can$225.00
Dr. Martens
Church Monkey booties
Men discounted price Can$220.00
Dr. Martens
2976 Blizzard WP Chelsea boots
Men discounted price Can$260.00
Dr. Martens
Boury utilitarian boots
Men discounted price Can$195.00
Dr. Martens
Boury utilitarian boots
Men discounted price Can$195.00
Dr. Martens
1460 WinterGrip lace-up boots
Men discounted price Can$260.00
Dr. Martens
Kip lace-up ankle boots
Men regular price $270.00 discounted price Can$199.95
Shoe The Bear
Stellan Chelsea boots
Men discounted price Can$245.00
Shoe The Bear
Stellan lined lace-up boots
Men regular price $260.00 discounted price Can$199.95
Shoe The Bear
Davis Square waterproof chukkas
Men discounted price Can$150.00
Timberland
Davis Square waterproof chukkas
Men discounted price Can$150.00
Timberland

New

Water-resistant Navi chukkas
Men discounted price Can$145.00
Toms
Standard Snow MTE winter boots
Men discounted price Can$235.00
Vans
Sk8-Hi GORE-TEX® MTE-3 winter sneakers
Men discounted price Can$225.00
Vans
Sk8-Hi DR MTE-2 winter sneakers
Men discounted price Can$190.00
Vans
UltraRange EXO Hi GORE-TEX MTE-3 boots
Men discounted price Can$260.00
Vans
Driftflex suede chukkas
Men discounted price Can$359.00
Astorflex
Online only
Dukeflex suede chukkas
Men discounted price Can$279.00
Astorflex
Online only
Greenflex suede chukkas
Men discounted price Can$259.00
Astorflex
Online only
Bitflex suede Chelsea boots
Men discounted price Can$299.00
Astorflex
Online only

Editor's pick

Bootflex suede ankle boots
Men discounted price Can$299.00
Astorflex
Online only
Velasca ankle boots
Men discounted price Can$395.00
WANT Les Essentiels
Online only
Wellington lined Chelsea boots
Men discounted price Can$395.00
WANT Les Essentiels
Online only
Montoro lugged derby boots
Men discounted price Can$425.00
WANT Les Essentiels
Online only
Fireburst winter boots
Men discounted price Can$235.00
Pajar Canada
Online only
Fero winter boots
Men discounted price Can$225.00
Pajar Canada
Online only
Mercer Alptreck ice-gripper winter boots
Men discounted price Can$325.00
Pajar Canada
Online only
Sarge ice-gripper winter combat boots
Men discounted price Can$350.00
Pajar Canada
Online only
Maddox ice-gripper winter boots
Men discounted price Can$340.00
Pajar Canada
Online only
Gavel pull-up winter boots
Men discounted price Can$235.00
Pajar Canada
Online only
Geotrecca RP water-resistant boots
Men discounted price Can$220.00
Teva
Online only
Flag of the United States

Are you in the United States?

Visit simons.com