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Men's Underwear

Featured

le 31 logo

Favourite Snacks Trunk

- Fun print
- Soft and stretchy organic cotton jersey

Men's boxer brief with funky prints at Simons
Microfibre athletic boxer brief discounted price Can$15.00
Le 31

Editor's pick

Solid viscose trunk discounted price Can$20.00
Le 31

New

Outdoor pattern boxer brief discounted price Can$20.00
Le 31
Large logo ivory trunk regular price $25.00 discounted price Can$19.99
Diesel
Striped-waistband organic cotton and TENCEL™ Modal boxer brief discounted price Can$15.00
3 for $34.95
Le 31
Favourite snacks trunk discounted price Can$20.00
Le 31

Sophisticated menswear with a touch of avant-garde, Le 31 appeals to the businessman, the innovator, the adventure-seeker, and the athlete with its wide range of collections that feature everything from the comfiest essentials to the season's trendiest pieces.

Editor's pick

Solid viscose trunk discounted price Can$20.00
Le 31
Feel tone-on-tone lyocell brief discounted price Can$29.00
2 for $39.95
Le 31

New

Contrast seam thick-waist brief discounted price Can$20.00
Le 31

New

Contrast seam thick-waist brief discounted price Can$20.00
Le 31

New

Contrast seam thick-waist brief discounted price Can$20.00
Le 31
Shiny microfibre brief discounted price Can$20.00
Le 31
Striped-waistband organic cotton and TENCEL™ Modal brief discounted price Can$15.00
3 for $34.95
Le 31
Shiny microfibre trunk discounted price Can$20.00
Le 31
Striped-waistband organic cotton and TENCEL™ Modal trunk discounted price Can$15.00
3 for $34.95
Le 31

Editor's pick

Solid viscose trunk discounted price Can$20.00
Le 31

Editor's pick

Solid viscose trunk discounted price Can$20.00
Le 31
Contrasting topstitch trunk discounted price Can$15.00
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
Micro-pattern recycled microfibre brief discounted price Can$25.00
3 for $49.95
Le 31
Mixed-stripe turquoise brief discounted price Can$25.00
3 for $49.95
Le 31
Patterned teal-waist brief discounted price Can$25.00
3 for $49.95
Le 31
Mixed-stripe turquoise trunk discounted price Can$25.00
3 for $49.95
Le 31
Micro-pattern recycled microfibre trunk discounted price Can$25.00
3 for $49.95
Le 31
Patterned teal-waist trunk discounted price Can$25.00
3 for $49.95
Le 31
Organic cotton and modal boxer briefs
3-pack
discounted price Can$45.00
Le 31
Organic cotton and modal boxer briefs
3-pack
discounted price Can$45.00
Le 31
Contrast-waist organic cotton trunks
3-pack
discounted price Can$39.95
Le 31
Solid organic cotton boxer briefs
3-pack
discounted price Can$39.95
Le 31
Stretch organic cotton briefs
3-pack
discounted price Can$29.95
Le 31
Solid organic cotton boxer briefs
3-pack
discounted price Can$39.95
Le 31
Organic cotton briefs
3-pack
discounted price Can$29.95
Le 31
Organic cotton briefs
3-pack
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
Mixed stripe viscose trunk regular price $25.00 discounted price Can$15.99
Le 31
Organic cotton ribbed brief regular price $25.00 discounted price Can$19.99
Le 31
Organic cotton ribbed legging regular price $49.00 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
Tone-on-tone Feel Lyocell trunk regular price $29.00 discounted price Can$19.99
Le 31
Organic cotton mesh brief regular price $25.00 discounted price Can$19.99
Le 31
Organic cotton mesh trunk regular price $25.00 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
Solid and striped essential boxer briefs
2-pack
regular price $40.00 discounted price Can$29.95
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $40.00 discounted price Can$29.95
Le 31
Jack & Jones at Simons

Founded in 1990 out of a love for denim, this European brand offers a complete range of clothing, underwear, and accessories for men.

Neon waist trunk discounted price Can$15.00
Jack & Jones
Dark floral trunk discounted price Can$15.00
Jack & Jones
Vivid colour trunk discounted price Can$15.00
Jack & Jones

New

Two-tone stripe trunk discounted price Can$15.00
Jack & Jones
Green-and-blue trunk discounted price Can$15.00
Jack & Jones

New

Two-tone stripe trunk discounted price Can$15.00
Jack & Jones

New

Yellow-accent navy trunk discounted price Can$15.00
Jack & Jones
Dark floral trunk discounted price Can$15.00
Jack & Jones
Signature black trunk discounted price Can$15.00
Jack & Jones
Black and lime-green trunk discounted price Can$15.00
Jack & Jones
Colourful skull trunk discounted price Can$15.00
Jack & Jones
Black and lime-green trunk discounted price Can$15.00
Jack & Jones
Navy-blue trunk discounted price Can$15.00
Jack & Jones
Colourful leaf trunk discounted price Can$15.00
Jack & Jones
Contrast waist trunk discounted price Can$15.00
Jack & Jones
Contrast waist trunk discounted price Can$15.00
Jack & Jones
Surrealist illustration trunk discounted price Can$15.00
Jack & Jones
Contrast waist trunk discounted price Can$15.00
Jack & Jones

Editor's pick

Minimalist solid trunk discounted price Can$15.00
Jack & Jones
Exotic jungle trunk discounted price Can$15.00
Jack & Jones
Lined waist blue trunk discounted price Can$15.00
Jack & Jones
Funky pattern trunk discounted price Can$15.00
Jack & Jones
Striped logo waist trunk discounted price Can$15.00
Jack & Jones
Tropical trunk discounted price Can$15.00
Jack & Jones
Jewel-toned waist trunk discounted price Can$15.00
Jack & Jones
Tiger trunk discounted price Can$15.00
Jack & Jones
Jewel-toned waist trunk discounted price Can$15.00
Jack & Jones
Tropical trunk discounted price Can$15.00
Jack & Jones
Jewel-toned waist trunk discounted price Can$15.00
Jack & Jones
Tropical trunk discounted price Can$15.00
Jack & Jones

New

Flamingo waist trunk discounted price Can$15.00
Jack & Jones
Navy and cyan trunk discounted price Can$15.00
Jack & Jones
Logo waist trunk discounted price Can$15.00
Jack & Jones

New

Contrast-waist navy-blue trunk discounted price Can$15.00
Jack & Jones
saxx logo

When it comes to underwear, think outside the box. With its 3D BallPark Pouch™ support system and its colourful, vibrant prints, this Canadian brand stands out both in terms of aesthetics and comfort.

SAXX boxer at Simons
Pink Hibiscus boxer brief
DROPTEMP™
discounted price Can$37.00
Saxx
Erik Abel sharks boxer brief
VIBE
discounted price Can$37.00
Saxx
Hawaiian pizza boxer brief
ULTRA
discounted price Can$37.00
Saxx
Sunset wave boxer brief
VIBE
discounted price Can$37.00
Saxx
Camo coolers boxer brief
DAYTRIPPER
discounted price Can$29.00
Saxx
Mini-stripe boxer brief
VIBE
discounted price Can$37.00
Saxx
Logo waist black trunk
VIBE
discounted price Can$36.00
Saxx
Solid light boxer brief
ULTRA
discounted price Can$37.00
Saxx
Camping toast boxer brief
ULTRA
regular price $37.00 discounted price Can$29.95
Saxx
Colourful illustration boxer brief
DAYTRIPPER
discounted price Can$29.00
Saxx
Solid boxer briefs
VIBE - 3-pack
discounted price Can$98.00
Saxx
Teal boxer brief
VIBE
discounted price Can$37.00
Saxx
Banana Split boxer brief
DROPTEMP™
regular price $37.00 discounted price Can$29.95
Saxx
Snowmobile yeti 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

Men's Boxers & Briefs

Whether you're working, training at the gym, or simply relaxing at home, comfort is a priority. And when it comes to comfort, choosing the right underwear is key. At Simons, we offer a wide variety of trunks, boxers, and boxer briefs to suit your every need.

 

Take your pick in our selection of high-quality, comfortable, and sometimes playful designs by Calvin Klein, Jack & Jones, BOSS by HUGO BOSS, SAXX, or our private brand, Le 31. Make sure to choose the fabric that's right for you. Your underwear should be stretchy and breathable. Cotton, modal, and bamboo rayon are particularly popular!

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