Skip to main content
The Simons members:
free shipping over $50 and free returns (exceptions may apply)
Men
Quick view Full details
1840 print T-shirt
Our History, Our Heritage Collection
Unisex discounted price Can$59.00
Simons
Quick view Full details
A Grand Voyage T-shirt
Our History, Our Heritage Collection
Unisex discounted price Can$69.00
Simons
Quick view Full details
1840 patch T-shirt
Our History, Our Heritage Collection
Unisex discounted price Can$59.00
Simons
Quick view Full details
1840 fleece-lined sweatshirt
Our History, Our Heritage Collection
Unisex discounted price Can$69.00
Simons
Quick view Full details
1840 embroidery fleece-lined sweatshirt
Our History, Our Heritage Collection
Unisex discounted price Can$69.00
Simons
Quick view Full details
100% organic cotton map hoodie
Our History, Our Heritage Collection
Unisex discounted price Can$89.00
Simons
Quick view Full details
Minimalist flip-flops
Exclusive collection from Italy discounted price Can$29.00
Simons
Quick view Full details
Colour block boat shoes regular price $175.00 discounted price Can$99.95
Simons
Quick view Full details
Brown leather notched boat shoes
Men regular price $175.00 discounted price Can$99.95
Simons
Quick view Full details
Sergio Western boots
Men discounted price Can$425.00
Simons
Quick view Full details
Santiago croc penny loafers
Men regular price $295.00 discounted price Can$199.95
Simons
Quick view Full details
Smooth leather derby shoes
Men discounted price Can$195.00
Simons
Quick view Full details
Smooth leather penny loafers
Men discounted price Can$225.00
Simons
Quick view Full details
Leather brogue shoe
Men discounted price Can$195.00
Simons
Quick view Full details

Editor's pick

Cotton scented candle discounted price Can$49.00
Simons
Quick view Full details

Editor's pick

Coton eau de parfum discounted price Can$69.00
Simons
Quick view Full details
1840 wool socks
Our History, Our Heritage Collection
Unisex discounted price Can$19.00
Simons
Quick view Full details
1840 zipped pouch
Our History, Our Heritage Collection discounted price Can$45.00
Simons
Quick view Full details
Organic cotton 1840 tote bag
Our History, Our Heritage Collection discounted price Can$69.00
Simons
Quick view Full details
1840 embroidery cap
Our History, Our Heritage Collection
Unisex discounted price Can$49.00
Simons
Quick view Full details
A Grand Voyage pure silk scarf
Our History, Our Heritage Collection
Unisex discounted price Can$49.00
Simons
Quick view Full details
1840 teddy bear charm
Our History, Our Heritage Collection discounted price Can$39.00
Simons
Quick view Full details
Signature green leaf charm
Our History, Our Heritage Collection discounted price Can$39.00
Simons
Quick view Full details
1840 leather luggage tag
Our History, Our Heritage Collection discounted price Can$39.00
Simons
Quick view Full details

Editor's pick

Vacation embroidery swim short regular price $59.00 discounted price Can$39.95
Simons
Quick view Full details
Colourful print swim short regular price $59.00 discounted price Can$39.95
Simons
+8
Quick view Full details

Editor's pick

Solid-coloured swim short regular price $39.00 discounted price Can$29.95
Simons
Quick view Full details
Printed stretch swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Monochrome stripe seersucker swim short regular price $59.00 discounted price Can$39.95
Simons
Quick view Full details

Editor's pick

Piped retro fitted swim trunk regular price $39.00 discounted price Can$24.95
Simons
Quick view Full details
Nautical stripe swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Contrast-lining solid stretch swim trunk regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details

Editor's pick

Crinkled-texture swim short discounted price Can$59.00
Simons
+3
Quick view Full details

Editor's pick

Striped seersucker swim short regular price $59.00 discounted price Can$39.95
Simons
Quick view Full details
Natural drawstring geo-pattern swim short discounted price Can$59.00
Simons
Quick view Full details

Editor's pick

Piped retro swim short discounted price Can$50.00
Simons
Quick view Full details
Embroidered cropped swim short regular price $79.00 discounted price Can$49.95
Simons
Quick view Full details

Editor's pick

Parasol-stripe swim short discounted price Can$59.00
Simons
Quick view Full details
Nautical stripe swim short discounted price Can$59.00
Simons
Quick view Full details
Printed stretch swim short discounted price Can$59.00
Simons
Quick view Full details
Printed fitted swim trunk discounted price Can$39.00
Simons
Quick view Full details
Monochrome swim brief discounted price Can$39.00
Simons
Quick view Full details
Nautical stripe swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Nautical stripe swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Peachskin recycled fibre swim short regular price $39.00 discounted price Can$19.99
Simons
Quick view Full details
Monochrome swim brief regular price $39.00 discounted price Can$19.99
Simons
Quick view Full details
Nautical stripe swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Nautical stripe swim short regular price $59.00 discounted price Can$29.95
Simons
Quick view Full details
Minimalist leather court sneakers
Men regular price $150.00 discounted price Can$99.95
Simons
Quick view Full details
Beige suede low-top sneakers
Men regular price $225.00 discounted price Can$99.95
Simons
Quick view Full details
Black leather and suede low sneakers
Men regular price $225.00 discounted price Can$99.95
Simons
Quick view Full details
Chocolate suede Dutch espadrilles
Men regular price $150.00 discounted price Can$99.95
Simons
Quick view Full details
Minimalist leather penny loafers
Men discounted price Can$195.00
Simons
Quick view Full details
Glossy leather penny loafers
Men discounted price Can$195.00
Simons
Quick view Full details
Leopard tassel loafers
Men regular price $250.00 discounted price Can$99.95
Simons
Quick view Full details
Suede penny loafers
Men discounted price Can$195.00
Simons
Quick view Full details
Snakeskin penny loafers
Men discounted price Can$225.00
Simons
Quick view Full details

New

Black Venetian loafers
Men discounted price Can$195.00
Simons
Quick view Full details

New

Suede derby shoes
Men discounted price Can$195.00
Simons
Quick view Full details
Contrast sole suede loafers
Men discounted price Can$175.00
Simons
Quick view Full details

New

Suede sand boat shoes discounted price Can$175.00
Simons
Quick view Full details
Santiago suede penny loafers
Men regular price $275.00 discounted price Can$199.95
Simons
Quick view Full details
Brown leather boat shoes
Men regular price $125.00 discounted price Can$99.95
Simons
Quick view Full details
Navy-blue suede boat shoes
Men regular price $125.00 discounted price Can$99.95
Simons
Quick view Full details
Sigrid square-toe boots
Men discounted price Can$295.00
Simons
Quick view Full details
Gordon derby shoes
Men regular price $195.00 discounted price Can$149.95
Simons
Quick view Full details
Chunky notched sole leather brogue shoes
Men regular price $225.00 discounted price Can$149.95
Simons