Skip to main content
The Simons members:
free shipping over $50 and free returns (exceptions may apply)
Shoes
Quick view Full details
Pix Berlin lace-up boots
Men discounted price Can$320.00
Camper
Quick view Full details
Wooster II suede derby shoes
Men discounted price Can$695.00
Scarosso
Quick view Full details
Alessandro horsebit loafers
Men discounted price Can$675.00
Scarosso
Quick view Full details
Alessandro croc-skin leather horsebit loafers
Men discounted price Can$695.00
Scarosso
Quick view Full details
Nimbus rubber Chelsea boots
Men discounted price Can$185.00
Barbour
Quick view Full details
Shep slipper loafers
Men discounted price Can$150.00
UGG
Quick view Full details
Tasman braided mule slippers
Men discounted price Can$250.00
UGG
Quick view Full details
Cloud 6 waterproof sneakers
Men discounted price Can$210.00
On
Quick view Full details
Augustus Chelsea boots
Men discounted price Can$450.00
PS Paul Smith
Quick view Full details

Editor's pick

Work sock bootie slippers
Men discounted price Can$50.00
Simons
Quick view Full details
Felted mule slippers
Men discounted price Can$39.00
Simons
Quick view Full details
Brown suede Dean derby shoes
Men discounted price Can$240.00
Camper
Quick view Full details
Cowhide-pattern fuzzy Otzo clogs
Men discounted price Can$230.00
UGG
Quick view Full details
Samba CLOT light pink sneakers
Men discounted price Can$180.00
Adidas x CLOT
Quick view Full details
Superstar 3G sneakers
Men discounted price Can$480.00
Y-3
Quick view Full details
EVO SL ATR GTX sneakers
Men discounted price Can$480.00
Y-3
Quick view Full details
Lee chocolate brown pebble leather sneakers
Men discounted price Can$395.00
PS Paul Smith
Quick view Full details
Nizzastar Hi sneakers
Men discounted price Can$500.00
Y-3
Quick view Full details
Samba CLOT mint green sneakers
Men discounted price Can$180.00
Adidas x CLOT
Quick view Full details
Albany black leather sneakers
Men discounted price Can$350.00
PS Paul Smith
Quick view Full details
Samba CLOT black-and-white sneakers
Men discounted price Can$180.00
Adidas x CLOT
Quick view Full details
Kieran brown leather sneakers
Men discounted price Can$249.00
BOSS
Quick view Full details
Distressed leather Sport clog
Men discounted price Can$240.00
Coach
Quick view Full details
Tasman Weather Hybrid boots
Men discounted price Can$185.00
UGG
Quick view Full details
Thermoball™ Basecamp™ mule slippers
Men discounted price Can$140.00
The North Face
Quick view Full details
Jeno pebbled leather Western boots
Men discounted price Can$375.00
Caborca
Quick view Full details
Wallabee brown beeswax leather shoes
Men discounted price Can$190.00
Clarks
Quick view Full details
Gahan Western Chelsea boots
Men discounted price Can$350.00
Caborca
Quick view Full details
Wallabee studded-detail suede shoes
Men discounted price Can$260.00
Clarks
Quick view Full details
Wallabee cow-print pony hair leather shoes
Men discounted price Can$250.00
Clarks
Quick view Full details
Relaxed leather boots
Men discounted price Can$550.00
Willy Chavarria x UGG
Quick view Full details
Otzo clog
Men discounted price Can$300.00
Willy Chavarria x UGG
Quick view Full details
Hotel mule slipper
Men discounted price Can$225.00
Willy Chavarria x UGG
Quick view Full details
Tucker oiled-leather boat shoes
Men discounted price Can$460.00
Sebago
Quick view Full details
Butterfly print derby shoes
Men discounted price Can$850.00
Undercover
Quick view Full details
Foldable black leather flats
Men discounted price Can$950.00
Jacquemus
Quick view Full details
Creeper Gabe boot
Men discounted price Can$2,900.00
Rick Owens
Quick view Full details
Megalace® Mega Tractor boots
Men discounted price Can$2,800.00
Rick Owens
Quick view Full details
Owen derby shoes
Men discounted price Can$258.00
Polo Ralph Lauren
Quick view Full details
Jett notched penny loafers
Men discounted price Can$258.00
Polo Ralph Lauren
Quick view Full details
Tone-on-tone logo flip-flops
Men discounted price Can$34.00
Havaianas
Quick view Full details
Ezra supple penny loafers
Men discounted price Can$500.00
Duke + Dexter
Quick view Full details
Heritage Aera brogue sneakers
Men discounted price Can$225.00
Polo Ralph Lauren
Quick view Full details
ThermoBall™ Traction V slippers
Men discounted price Can$95.00
The North Face
Quick view Full details
Nimbus Cloud 574 sneakers
Men discounted price Can$130.00
New Balance
Quick view Full details
Acadia Artisan fringed boat shoes
Men discounted price Can$480.00
Sebago
Quick view Full details
Wilde Midnight Chateau penny loafers
Men discounted price Can$550.00
Duke + Dexter
Quick view Full details
Ricardo minimalist leather sneakers discounted price Can$225.00
Simons
Quick view Full details
Wilde Shewbacca pony-hair-leather penny loafers
Men discounted price Can$550.00
Duke + Dexter
Quick view Full details
M121 Commando hiking shoes
Men discounted price Can$650.00
Simons x Fracap
Quick view Full details
Dwarf lace-up boots
Men discounted price Can$295.00
Simons
Quick view Full details
Silvio square-toe mules
Men discounted price Can$250.00
Simons
Quick view Full details
Wilde distressed-leather penny loafers
Men discounted price Can$500.00
Duke + Dexter
Quick view Full details
Giant notched penny loafers
Men discounted price Can$195.00
Simons
Quick view Full details
Willis thready penny loafers
Men discounted price Can$425.00
Duke + Dexter
Quick view Full details
Hyperboost Edge H.Koumori sneakers
Men discounted price Can$260.00
Adidas x Hermanos Koumori
Quick view Full details
Adizero EVO SL H.Koumori sneakers
Men discounted price Can$180.00
Adidas x Hermanos Koumori
Quick view Full details
Amsterdam Wrapped suede mules
Men discounted price Can$180.00
Birkenstock
Quick view Full details
Navy suede Authentic sneakers
Men discounted price Can$90.00
Vans
Quick view Full details
Logo strap flip-flops
Men discounted price Can$45.00
Havaianas
Quick view Full details
Minimalist derby shoes
Men discounted price Can$449.00
BOSS
Quick view Full details
GrandPrø Angleace sneakers
Men discounted price Can$220.00
Cole Haan
Quick view Full details
Metallized initials khaki leather loafers
Men discounted price Can$1,000.00
Acne Studios
Quick view Full details
Square-toe suede boots
Men discounted price Can$1,400.00
Acne Studios
Quick view Full details
SFTM X Adirun01 Supernova Rise 3 sneakers
Men discounted price Can$190.00
Adidas X Song for the Mute
Quick view Full details
Square-toe suede penny loafers
Men discounted price Can$1,100.00
JW Anderson
Quick view Full details
Handball Spezial crackled leather sneakers
Men discounted price Can$140.00
Adidas Originals
Quick view Full details
Handball Spezial cocoa penny loafers
Men discounted price Can$150.00
Adidas Originals
Quick view Full details
LX Authentic 44 mixed-media sneakers
Men discounted price Can$125.00
Vans
Quick view Full details
Roundhill Grand waterproof Chelsea boots
Men discounted price Can$340.00
Cole Haan
Quick view Full details
Air Max 90 Premium green and white sneakers
Men discounted price Can$165.00
Nike
Quick view Full details
Dunk Low Retro snakeskin accent sneakers
Men discounted price Can$165.00
Nike
Quick view Full details
Burgundy logo Campo sneakers
Men discounted price Can$210.00
Veja
Quick view Full details
Cloudtilt sneakers
Men discounted price Can$200.00
On
Quick view Full details
Pierce suede penny loafers
Men discounted price Can$395.00
PS Paul Smith
Quick view Full details
Wide-toe leather derby shoes
Men discounted price Can$1,200.00
JW Anderson
Quick view Full details
Swan monochromatic sneakers
Men discounted price Can$950.00
Balmain
Quick view Full details
Timberland x Jacquemus boat shoe
Men discounted price Can$350.00
Jacquemus x Timberland
Quick view Full details
Ochre soft suede Boston mules
Men discounted price Can$205.00
Birkenstock
Quick view Full details
1978 gathered loafers
Men discounted price Can$330.00
Camperlab
Quick view Full details
BW Army sneakers
Men discounted price Can$160.00
Adidas Originals
Quick view Full details
Toscano Volanto M140 hiking boots
Men discounted price Can$750.00
Simons x Fracap
Quick view Full details
Contrast logo V-90 O.T. sneakers
Men discounted price Can$255.00
Veja
Quick view Full details
Taupe suede GT sneakers
Men discounted price Can$220.00
Veja
Quick view Full details
Windham Grand waterproof Chelsea boots
Men discounted price Can$295.00
Cole Haan
Quick view Full details
Dean Grand derby shoes
Men discounted price Can$310.00
Cole Haan