Skip to main content
The Simons members:
free shipping over $50 and free returns (exceptions may apply)
Underwear & Leisurewear
Quick view Full details
3" black/navy/blue trunks
3-pack discounted price Can$58.00
Diesel
Quick view Full details
6" cotton boxer briefs
24SEVEN COTTON
3-pack discounted price Can$50.00
Saxx
Quick view Full details
2.5" oversized-logo trunk
Cotton discounted price Can$25.00
Diesel
Quick view Full details
3" logo-waist colourful trunk
Cotton discounted price Can$25.00
Diesel
Quick view Full details
Oversized-logo thong
Cotton discounted price Can$25.00
Diesel
Quick view Full details
6" stretch boxer briefs
DROPTEMP™
3-pack discounted price Can$70.00
Saxx
Quick view Full details
Black undershirts
DROPTEMP™
2-pack discounted price Can$47.00
Saxx
Quick view Full details
V-neck undershirt discounted price Can$48.00
Le 31
Quick view Full details
3" stretch trunk discounted price Can$35.00
Paul Smith
Quick view Full details
3" black/navy/green trunks
3-pack discounted price Can$60.00
Lacoste
Quick view Full details
3" colourful trunk
Cotton discounted price Can$25.00
Lacoste
Quick view Full details
Preppy striped loose trunk discounted price Can$45.00
Polo Ralph Lauren
Quick view Full details
6" black/light grey/dark grey boxer briefs
3-pack discounted price Can$80.00
Polo Ralph Lauren
Quick view Full details
4.5" black/purple/grey 100% cotton boxer briefs
Cotton
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
2.5" khaki/black/caramel low-rise trunks
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
5" grey/dotted/white stretch microfibre boxer briefs
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
2.5" low-rise grey/navy/white trunks
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
4" light-blue/striped/black 100% cotton boxer briefs
Cotton
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
Light-blue/striped/black 100% cotton briefs
3-pack discounted price Can$65.00
Calvin Klein
Quick view Full details
5" micro-perforated boxer brief
Nylon discounted price Can$45.00
Polo Ralph Lauren
Quick view Full details
Wintry teddy bear loose trunk
Cotton discounted price Can$45.00
Polo Ralph Lauren
Quick view Full details
6.5" ultra-comfortable jersey boxer brief discounted price Can$30.00
Polo Ralph Lauren
Quick view Full details
3.5" hot dog trunk
Cotton discounted price Can$15.00
Jack & Jones
Quick view Full details
4" ultra-comfortable boxer brief
Cotton discounted price Can$15.00
Jack & Jones
Quick view Full details
5" nautical stripes boxer brief discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
Nautical stripe brief
TENCEL™ modal & organic cotton discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
3" nautical stripe trunk
TENCEL™ modal & organic cotton discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
5" embroidered logo boxer briefs
Cotton
3-pack discounted price Can$70.00
Polo Ralph Lauren
Quick view Full details
5" colourful stretch jersey boxer brief
TENCEL™ modal & organic cotton discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
3" colourful stretch jersey trunk
TENCEL™ modal & organic cotton discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
Colourful stretch jersey brief
TENCEL™ modal & organic cotton discounted price Can$20.00
4 for $39.95
Le 31
Quick view Full details
Fair Isle wool socks discounted price Can$19.00
Le 31
Quick view Full details
Everyday Elevated colourful ankle socks
Set of 6 discounted price Can$34.00
Nike
Quick view Full details
Pinstripe bamboo dress socks discounted price Can$12.00
Lindbergh
Quick view Full details
Everyday Elevated socks
Set of 6 discounted price Can$34.00
Nike
Quick view Full details
Diamond dress socks
3-pack discounted price Can$28.00
Polo Ralph Lauren
Quick view Full details
Stretch ribbed tank undershirt discounted price Can$25.00
Le 31
+2
Quick view Full details
Solid bamboo viscose dress socks discounted price Can$12.00
Lindbergh
Quick view Full details
Contrast-trim lounge short discounted price Can$149.00
BOSS
Quick view Full details
Beckett cozy plush robe discounted price Can$195.00
UGG
Quick view Full details
Contrast trim zipped hoodie discounted price Can$199.00
BOSS
Quick view Full details
Long-sleeve T-shirt discounted price Can$39.00
Le 31
Quick view Full details
Navy stripe pyjama set discounted price Can$95.00
Lindbergh
Quick view Full details
Tasman mule slippers
Men discounted price Can$150.00
UGG
Quick view Full details
Everyday Elevated neutral ankle socks
Set of 6 discounted price Can$34.00
Nike
Quick view Full details
Everyday Elevated ped socks
Set of 6 discounted price Can$34.00
Nike
Quick view Full details
Chevron and stripe dress socks
3-pack discounted price Can$28.00
Polo Ralph Lauren
Quick view Full details
Blue stripe socks discounted price Can$24.00
Stance
Quick view Full details
Varsity striped socks discounted price Can$31.00
Stance
Quick view Full details
Colourful socks discounted price Can$22.00
Stance
Quick view Full details
Ultra-soft herringbone bathrobe discounted price Can$100.00
Le 31
Quick view Full details
Beige stripe socks discounted price Can$24.00
Stance
Quick view Full details
Mushroom dress socks discounted price Can$21.00
Bleuforêt
Quick view Full details
Everyday Elevated neutral socks
6-pack discounted price Can$34.00
Nike
Quick view Full details
Multicolour stripe sock discounted price Can$24.00
Stance
Quick view Full details
Owl dress socks discounted price Can$21.00
Bleuforêt
Quick view Full details
Mini-embroidery lounge T-shirt discounted price Can$39.00
Lindbergh
Quick view Full details
Pure cotton undershirt tank discounted price Can$30.00
BOSS
Quick view Full details
3" red/blue/black trunks
Dri-FIT Essential Micro
3-pack discounted price Can$63.00
Nike
Quick view Full details
Jacquard leopard socks discounted price Can$22.00
Le 31
Quick view Full details
Merino wool heather socks
Exclusive collection from Italy discounted price Can$34.00
Le 31
Quick view Full details
Wolves dress socks discounted price Can$21.00
Bleuforêt
Quick view Full details
Monochrome-stripe dress socks discounted price Can$20.00
Bleuforêt
Quick view Full details
Toy Story socks
4-pack discounted price Can$130.00
Stance
Quick view Full details
Coloured-dot dress socks discounted price Can$20.00
Bleuforêt
Quick view Full details
Jessie socks discounted price Can$31.00
Stance
Quick view Full details
Solid/mini-pattern dress socks
2-pack discounted price Can$29.00
BOSS
Quick view Full details
Solid/dotted dress socks
2-pack discounted price Can$30.00
BOSS
Quick view Full details
Two-tone stripe socks discounted price Can$23.00
Stance
Quick view Full details
Woody socks discounted price Can$31.00
Stance
Quick view Full details
Martini black socks discounted price Can$24.00
Stance
Quick view Full details
Buzz Lightyear socks discounted price Can$31.00
Stance
Quick view Full details
Solid stretch ankle socks
3-pack discounted price Can$19.00
Le 31
Quick view Full details
Pin dot bamboo dress socks discounted price Can$12.00
Lindbergh
Quick view Full details
Ribbed merino socks discounted price Can$19.00
Lindbergh
Quick view Full details
Minimalist dress socks
3-pack discounted price Can$34.00
BOSS
Quick view Full details
6" geo-patterned boxer brief
DROPTEMP™ discounted price Can$38.00
Saxx
Quick view Full details
6" fish micro-dotwork boxer brief
QUEST discounted price Can$38.00
Saxx
Quick view Full details
6" arabesque fish boxer brief
DROPTEMP™ discounted price Can$38.00
Saxx
Quick view Full details
6" pickle ball boxer brief
VIBE XTRA discounted price Can$38.00
Saxx
Quick view Full details
6" legendary dragon boxer brief
VIBE XTRA discounted price Can$38.00
Saxx
Quick view Full details
Exotic foliage 6" boxer brief
DROPTEMP™ discounted price Can$38.00
Saxx
Quick view Full details
6" bison with chain boxer brief
VIBE XTRA discounted price Can$38.00
Saxx
Quick view Full details
4" striped-waist boxer briefs
TENCEL™ modal & organic cotton
3-pack discounted price Can$49.00
Le 31
+2
Quick view Full details
5" microfibre athletic boxer brief
Retransformed polyester discounted price Can$20.00
3 for $34.95
Le 31
+2
Quick view Full details
3" microfibre athletic trunk
Retransformed polyester discounted price Can$20.00
3 for $34.95
Le 31
Quick view Full details
Sporty microfibre brief
Retransformed polyester discounted price Can$20.00
3 for $34.95
Le 31
Quick view Full details
Striped merino wool-blend socks discounted price Can$19.00
Le 31
Quick view Full details
Colourful dot merino wool-blend socks discounted price Can$19.00
Le 31
+3
Quick view Full details
Responsible merino wool blend socks discounted price Can$19.00
Le 31
Quick view Full details
Eagle Fieltro mule slippers
Men discounted price Can$69.00
Verbenas
Quick view Full details
Jacquard flower socks discounted price Can$22.00
Le 31
Quick view Full details
Colourful stripe sock discounted price Can$18.00
Le 31
Quick view Full details
Mini-heart socks discounted price Can$22.00
Le 31
Quick view Full details
Fish socks discounted price Can$22.00
Le 31
Quick view Full details
Jacquard dot socks discounted price Can$18.00
Le 31
Quick view Full details
Dachshunds socks discounted price Can$22.00
Le 31
Quick view Full details
Finely ribbed merino wool socks discounted price Can$25.00
Bleuforêt
Quick view Full details
Seamless Egyptian cotton dress socks discounted price Can$21.00
Bleuforêt
Flag of the United States

Are you in the United States?

Visit simons.com