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Featured

+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price Can$15.99
Le 31

3 for $34.95

Editor's pick

Bright microfibre trunk discounted price Can$15.00
3 for $34.95
Le 31

Editor's pick

Bright microfibre trunk discounted price Can$15.00
3 for $34.95
Le 31

Editor's pick

Bright microfibre trunk discounted price Can$15.00
3 for $34.95
Le 31

3 for $39.95

Bright organic cotton trunk discounted price Can$20.00
3 for $39.95
Le 31
Bright organic cotton trunk discounted price Can$20.00
3 for $39.95
Le 31
Bright organic cotton trunk discounted price Can$20.00
3 for $39.95
Le 31

Most popular trunks

Contrast-line TENCEL* Modal trunk regular price $20.00 discounted price Can$15.99
Le 31
Contrast-line TENCEL* Modal trunk regular price $20.00 discounted price Can$15.99
Le 31
Contrast-line TENCEL* Modal trunk regular price $20.00 discounted price Can$15.99
Le 31
Festive print trunk discounted price Can$20.00
Le 31
Foliage trunk discounted price Can$20.00
Le 31
Colourful snack trunk discounted price Can$20.00
Le 31
Colourful snack trunk discounted price Can$20.00
Le 31
Festive print trunk discounted price Can$20.00
Le 31
Colourful print TENCEL* Modal trunk discounted price Can$20.00
Le 31

Most popular boxer briefs

Mirage boxer brief
VIBE
discounted price Can$36.00
Saxx
Earthy boxer brief
VIBE
discounted price Can$36.00
Saxx
Nautical stripe boxer brief
VIBE
discounted price Can$36.00
Saxx
Mini-stripe boxer brief
VIBE
discounted price Can$36.00
Saxx

Editor's pick

Woodland camo boxer brief
VIBE
discounted price Can$36.00
Saxx
Butterfly palm boxer brief
VIBE
discounted price Can$36.00
Saxx

Most popular briefs

Tone-on-tone Feel lyocell brief discounted price Can$29.00
Le 31
Tone-on-tone Feel lyocell brief discounted price Can$29.00
Le 31
Tone-on-tone Feel lyocell brief discounted price Can$29.00
Le 31
Navy stripe brief regular price $20.00 discounted price Can$15.99
Le 31
Boreal stripe brief regular price $20.00 discounted price Can$15.99
Le 31
Contrast stripe brief regular price $20.00 discounted price Can$15.99
Le 31

Most popular multi-packs

Solid organic cotton boxer briefs
2-pack
discounted price Can$22.95
Le 31
Classic organic cotton boxer briefs
2-pack
discounted price Can$22.95
Le 31
Classic stretch cotton boxer briefs
3-pack
discounted price Can$48.00
Calvin Klein
Classic microfibre trunks
3-pack
discounted price Can$54.00
Calvin Klein
Classic stretch cotton trunks
3-pack
discounted price Can$48.00
Calvin Klein
Classic microfibre boxer briefs
3-pack
discounted price Can$54.00
Calvin Klein

Most popular boxers

Twin-stripe loose boxer discounted price Can$29.00
Le 31
Twin-stripe loose boxer discounted price Can$29.00
Le 31
Patterned loose boxer discounted price Can$29.00
Le 31

Most popular tanks & T-shirts

Organic cotton V-neck lounge T-shirt
2-pack
discounted price Can$24.95
Le 31
Classic ribbed tanks
3-pack
discounted price Can$48.00
Calvin Klein
Classic crew-neck T-shirts
3-pack
discounted price Can$48.00
Calvin Klein

Trunks

Colour block trunk discounted price Can$20.00
Le 31
Colour block trunk discounted price Can$20.00
Le 31
Colour block trunk discounted price Can$20.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price Can$29.00
Le 31

Editor's pick

Colourful bamboo rayon trunk discounted price Can$15.00
Le 31
Striped-waistband microfibre trunk regular price $15.00 discounted price Can$9.99
Le 31
Contrast topstitch trunk discounted price Can$15.00
Le 31
Sports club trunk discounted price Can$20.00
Le 31
Denim-like trunk discounted price Can$20.00
Le 31

New

Graded pastel trunk discounted price Can$20.00
Le 31
Recycled micro nylon trunk discounted price Can$20.00
Le 31
Words of love trunk regular price $20.00 discounted price Can$9.99
Le 31
Contrast stripe trunk regular price $20.00 discounted price Can$15.99
Le 31
Boreal stripe trunk regular price $20.00 discounted price Can$15.99
Le 31
Vertical blue stripe trunk discounted price Can$20.00
Le 31
Athletic stripe trunk regular price $20.00 discounted price Can$15.99
Le 31
Micro-zigzag trunk regular price $20.00 discounted price Can$15.99
Le 31
Hatched stripe trunk discounted price Can$20.00
Le 31
Geometric shape trunk discounted price Can$20.00
Le 31

New

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

New

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

New

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

New

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

New

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

New

Skeleton surfer trunk discounted price Can$15.00
Jack & Jones

New

Tropical skull trunk discounted price Can$15.00
Jack & Jones

New

Tropical hue trunk discounted price Can$15.00
Jack & Jones

New

Tropical hue trunk discounted price Can$15.00
Jack & Jones
Surf print band trunk discounted price Can$15.00
Jack & Jones
Surf print band trunk discounted price Can$15.00
Jack & Jones
Tropical flora trunk discounted price Can$15.00
Jack & Jones
Tropical flora trunk discounted price Can$15.00
Jack & Jones

New

Exotic-band trunk discounted price Can$15.00
Jack & Jones
Tropical flora trunk discounted price Can$15.00
Jack & Jones

New

Graphic band trunk discounted price Can$15.00
Jack & Jones
Graffiti logo trunk discounted price Can$15.00
Jack & Jones
Paradise blue trunk discounted price Can$15.00
Jack & Jones
Neon skull trunk discounted price Can$15.00
Jack & Jones
Tropical flamingo trunk discounted price Can$15.00
Jack & Jones
Neon skull trunk discounted price Can$15.00
Jack & Jones
Solid and patterned trunk discounted price Can$15.00
Jack & Jones
Logo waist trunk discounted price Can$15.00
Jack & Jones
Signature waist trunk discounted price Can$15.00
Jack & Jones
Signature waist trunk discounted price Can$15.00
Jack & Jones
Bright colour trunk discounted price Can$15.00
Jack & Jones
Logo belt trunk discounted price Can$15.00
Jack & Jones
Signature waist trunk discounted price Can$15.00
Jack & Jones
Monochrome microfibre trunk discounted price Can$15.00
Jack & Jones
Signature solid trunk discounted price Can$16.00
Guess
Contrast-waist orange trunk discounted price Can$16.00
Guess
Contrast-waist orange trunk discounted price Can$16.00
Guess
Beer Pong trunk
VIBE
discounted price Can$36.00
Saxx
Logo waist solid trunk
VIBE
discounted price Can$36.00
Saxx

Editor's pick

Slim fit trunk discounted price Can$32.00
JM

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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