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Featured

Retro stripe trunk discounted price Can$25.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price Can$29.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price Can$29.00
Le 31

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
Bright organic cotton trunk discounted price Can$20.00
3 for $34.95
Le 31
Bright organic cotton trunk discounted price Can$20.00
3 for $34.95
Le 31
Bright organic cotton trunk discounted price Can$20.00
3 for $34.95
Le 31

Most popular trunks

+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
Contrast-line modal trunk regular price $20.00 discounted price Can$15.99
Le 31
Contrast-line modal trunk regular price $20.00 discounted price Can$15.99
Le 31
Contrast-line modal trunk regular price $20.00 discounted price Can$15.99
Le 31

New

Solid viscose trunk discounted price Can$20.00
Le 31
Foliage trunk regular price $20.00 discounted price Can$15.99
Le 31
Colourful snack trunk regular price $20.00 discounted price Can$15.99
Le 31

Most popular boxer briefs

Grillicious boxer brief
VIBE
discounted price Can$36.00
Saxx
Nautical stripe boxer brief
VIBE
discounted price Can$36.00
Saxx

Editor's pick

Woodland camo boxer brief
VIBE
discounted price Can$36.00
Saxx
Earthy boxer brief
VIBE
discounted price Can$36.00
Saxx

New

Midnight Tropics boxer brief
VIBE
discounted price Can$36.00
Saxx
Mini-stripe 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

New

Contrast-seam solid brief discounted price Can$20.00
Le 31

New

Contrast-seam solid brief discounted price Can$20.00
Le 31

New

Contrast-seam solid brief discounted price Can$20.00
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$54.00
Calvin Klein
Classic microfibre trunks
3-pack
discounted price Can$60.00
Calvin Klein
Classic stretch cotton trunks
3-pack
discounted price Can$54.00
Calvin Klein
Classic microfibre boxer briefs
3-pack
discounted price Can$60.00
Calvin Klein

Most popular boxers

New

Organic cotton flannel loose trunk discounted price Can$29.00
Le 31
Loose organic cotton jersey boxer regular price $20.00 discounted price Can$15.99
Le 31

New

Organic cotton flannel loose trunk 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$54.00
Calvin Klein
Classic crew-neck T-shirts
3-pack
discounted price Can$54.00
Calvin Klein

Trunks

Denim-like trunk regular price $20.00 discounted price Can$12.99
Le 31

Editor's pick

Bright microfibre trunk regular price $15.00 discounted price Can$9.99
Le 31
Graded pastel trunk regular price $20.00 discounted price Can$5.99
Le 31
Colour block trunk regular price $20.00 discounted price Can$15.99
Le 31
Colour block trunk regular price $20.00 discounted price Can$15.99
Le 31
Sports club trunk regular price $20.00 discounted price Can$15.99
Le 31
Nautical stripe trunk discounted price Can$20.00
3 for $39.95
Le 31
Hatched stripe trunk discounted price Can$20.00
3 for $39.95
Le 31
Burgundy stripe trunk discounted price Can$20.00
3 for $39.95
Le 31
Heather grey trunk discounted price Can$20.00
3 for $39.95
Le 31
Vertical blue stripe trunk discounted price Can$20.00
3 for $39.95
Le 31
Geometric shape trunk discounted price Can$20.00
3 for $39.95
Le 31

Editor's pick

Colourful bamboo rayon trunk discounted price Can$15.00
Le 31
Festive print trunk discounted price Can$20.00
Le 31
Recycled micro nylon trunk discounted price Can$20.00
Le 31
Sports club trunk discounted price Can$20.00
Le 31

New

Saturated foliage trunk discounted price Can$15.00
Jack & Jones

New

Saturated foliage trunk discounted price Can$15.00
Jack & Jones

New

Funky camo trunk discounted price Can$15.00
Jack & Jones

New

Funky camo trunk discounted price Can$15.00
Jack & Jones

New

Contrast foliage trunk discounted price Can$15.00
Jack & Jones

New

Contrast foliage trunk discounted price Can$15.00
Jack & Jones
Two-tone band trunk discounted price Can$15.00
Jack & Jones
Two-tone band trunk discounted price Can$15.00
Jack & Jones
Two-tone band trunk discounted price Can$15.00
Jack & Jones
Graffiti globe trunk discounted price Can$15.00
Jack & Jones
Yellow graffiti trunk discounted price Can$15.00
Jack & Jones
Vivid colours trunk discounted price Can$15.00
Jack & Jones
Vivid colours trunk discounted price Can$15.00
Jack & Jones
Monochrome microfibre trunk discounted price Can$15.00
Jack & Jones
Tropical hue trunk discounted price Can$15.00
Jack & Jones
Dotted hatched logo trunk discounted price Can$15.00
Jack & Jones
Logo waist 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
Beer Pong trunk
VIBE
discounted price Can$36.00
Saxx
Logo waist solid trunk
VIBE
discounted price Can$36.00
Saxx
TENCEL* Lyocell solid trunk regular price $39.00 discounted price Can$19.99
Organic Basics

Editor's pick

Slim fit trunk discounted price Can$32.00
JM

Editor's pick

Slim fit trunk discounted price Can$32.00
JM
Second skin trunk discounted price Can$28.00
JM
Solid pop-coloured trunk regular price $30.00 discounted price Can$19.99
Calvin Klein
Solid pop-coloured trunk regular price $30.00 discounted price Can$19.99
Calvin Klein
Solid pop-coloured trunk regular price $30.00 discounted price Can$19.99
Calvin Klein
Solid pop-coloured trunk regular price $30.00 discounted price Can$19.99
Calvin Klein
Watermelon trunk regular price $35.00 discounted price Can$15.99
Diesel
Tropical pattern double trunk discounted price Can$50.00
Diesel
Red detail trunk regular price $38.00 discounted price Can$25.95
Diesel

New

Abstract camo trunk discounted price Can$52.00
BOSS
Blue repeat-logo trunk regular price $42.00 discounted price Can$25.95
BOSS
Blue scale trunk discounted price Can$52.00
BOSS
Trimmed logo trunk discounted price Can$42.00
BOSS
Mint green logo trunk regular price $42.00 discounted price Can$25.95
BOSS

New

Flecked green trunk discounted price Can$52.00
BOSS

New

Monogram trunk discounted price Can$42.00
BOSS

New

Geo print trunk discounted price Can$42.00
BOSS
Working from home trunk regular price $65.00 discounted price Can$39.95
Paul Smith

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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