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

Underwear On Promo

For a limited time, take advantage of our special offers on all your favourite styles.

3 for $34.95

Contrasting topstitch trunk discounted price Can$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price Can$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price Can$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price Can$15.00
3 for $34.95
Le 31
Contrasting topstitch trunk discounted price Can$15.00
3 for $34.95
Le 31
Exotic jungle trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Colourful band black trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Signature waist trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Signature waist trunk discounted price Can$15.00
3 for $34.95
Jack & Jones

Editor's pick

Large dot trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Orange-waist navy trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Vivid colour trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Neon foliage trunk discounted price Can$15.00
3 for $34.95
Jack & Jones

Editor's pick

Minimalist solid trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Tropical trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Lined waist blue trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Neon waist trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Logo waist trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Funky pattern trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Green-and-blue trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Surrealist illustration trunk discounted price Can$15.00
3 for $34.95
Jack & Jones
Colourful skull trunk discounted price Can$15.00
3 for $34.95
Jack & Jones

2 for $39.95

Feel tone-on-tone lyocell brief discounted price Can$29.00
2 for $39.95
Le 31
Feel tone-on-tone lyocell brief discounted price Can$29.00
2 for $39.95
Le 31
Feel tone-on-tone lyocell brief discounted price Can$29.00
2 for $39.95
Le 31
Feel tone-on-tone lyocell brief discounted price Can$29.00
2 for $39.95
Le 31

Individual Item Promos

Mixed stripe viscose trunk regular price $25.00 discounted price Can$15.99
Le 31
Striped grey trunk regular price $20.00 discounted price Can$15.99
Le 31
Red stripe brief regular price $20.00 discounted price Can$15.99
Le 31
Red stripe trunk regular price $20.00 discounted price Can$15.99
Le 31
Organic cotton mesh trunk regular price $25.00 discounted price Can$19.99
Le 31
Organic cotton mesh brief regular price $25.00 discounted price Can$19.99
Le 31
Tone-on-tone Feel Lyocell boxer brief regular price $29.00 discounted price Can$19.99
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $40.00 discounted price Can$29.95
Le 31
Tone-on-tone Feel Lyocell trunk regular price $29.00 discounted price Can$19.99
Le 31
Organic cotton ribbed legging regular price $49.00 discounted price Can$29.95
Le 31

Editor's pick

Organic cotton ribbed tank regular price $39.00 discounted price Can$29.95
Le 31
Organic cotton ribbed brief regular price $25.00 discounted price Can$19.99
Le 31
Large logo ivory trunk regular price $25.00 discounted price Can$19.99
Diesel
Contrast waist and seam trunk regular price $25.00 discounted price Can$19.99
Diesel
Repeated logo briefs
3-pack
regular price $59.00 discounted price Can$39.95
Lacoste
Croc logo boxer brief regular price $25.00 discounted price Can$19.99
Lacoste
Dri-FIT ReLuxe heathered-waist boxer briefs
2-pack
regular price $52.00 discounted price Can$39.95
Nike
Dri-FIT Everyday pop band boxer briefs
3-pack
regular price $52.00 discounted price Can$39.95
Nike
Colourful band pure cotton boxer briefs
5-pack
regular price $82.00 discounted price Can$59.95
Calvin Klein
Black Reconsidered Steel trunks
3-pack
regular price $74.00 discounted price Can$49.95
Calvin Klein
Logo-waist blue brief regular price $20.00 discounted price Can$15.99
Tommy Hilfiger
Mini-check poplin boxer brief regular price $25.00 discounted price Can$19.99
Tommy Hilfiger
Twin stripe poplin boxer brief regular price $25.00 discounted price Can$19.99
Tommy Hilfiger
Embroidered logo loose poplin trunk regular price $32.00 discounted price Can$19.99
Polo Ralph Lauren
Animal hockey player boxer brief
VIBE
regular price $37.00 discounted price Can$19.99
Saxx
Snowmobile yeti boxer brief
VIBE
regular price $37.00 discounted price Can$29.95
Saxx
Season Pass boxer brief
DROPTEMP™
regular price $37.00 discounted price Can$29.95
Saxx
Banana Split boxer brief
DROPTEMP™
regular price $37.00 discounted price Can$29.95
Saxx
Gaming boxer brief
ULTRA
regular price $37.00 discounted price Can$19.99
Saxx
Hot dog boxer brief
VIBE
regular price $37.00 discounted price Can$29.95
Saxx
Pixelated football boxer brief
ULTRA
regular price $37.00 discounted price Can$29.95
Saxx
Pixel and solid boxer briefs
DAYTRIPPER - 2-pack
regular price $52.00 discounted price Can$39.95
Saxx
Colourful-waist trunk regular price $25.00 discounted price Can$19.99
BOSS
Velvet trunk regular price $45.00 discounted price Can$19.99
2(x)ist
Snakeskin pattern trunk regular price $55.00 discounted price Can$19.99
2(x)ist

Editor's pick

Twin-stripe brief regular price $20.00 discounted price Can$5.99
Le 31
Flag of the United States

Are you in the United States?

Visit simons.com