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Underwear - masculine underwear & loungewear
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Most popular boxers trunks

Editor's pick
Get Lucky trunk Can$20.00 Can$12.99
Le 31
Loft trunk Can$20.00 Can$12.99
Le 31
Leopard trunk Can$20.00
Le 31

Most popular boxers briefs

Mini logo boxer brief Can$20.00 Can$14.99
Champion
Iconic logo boxer brief Can$20.00 Can$14.99
Champion
Multi-logo trunk Can$20.00 Can$14.99
Champion
Mini logo boxer brief Can$20.00 Can$14.99
Champion
Multi-logo trunk Can$20.00 Can$14.99
Champion

Most popular slips

Most popular multi-packs

Editor's pick
Playful pattern trunk
2-pack
Can$30.00 Can$19.99
Le 31
Editor's pick
Playful pattern trunk
2-pack
Can$30.00 Can$19.99
Le 31
Accent seam trunk
2-pack
Can$30.00 Can$19.99
Le 31
Accent seam trunk
2-pack
Can$30.00 Can$19.99
Le 31
Accent seam trunk
2-pack
Can$30.00 Can$19.99
Le 31

Most popular tanks & T-shirts

Ribbed tank 3-pack Can$48.00
Calvin Klein
Essential bamboo lounge T-shirt Can$25.00 Can$19.99
Le 31
Bamboo crew-neck T-shirt Can$20.00 Can$12.99
Le 31

Trunks

Editor's pick
Bamboo rayon trunk Can$15.00 Can$9.99
Le 31
Editor's pick
Bamboo rayon trunk Can$15.00 Can$9.99
Le 31
Athletic-stripe floral trunk Can$20.00 Can$14.99
Le 31
International boxer brief Can$20.00 Can$9.99
Le 31
Treats trunk Can$20.00 Can$12.99
Le 31
Treats trunk Can$20.00 Can$12.99
Le 31
Treats trunk Can$20.00 Can$12.99
Le 31
Arcade trunk Can$20.00 Can$12.99
Le 31
Micro chalet patterned trunk Can$20.00 Can$12.99
Le 31
Nocturnal foliage trunk Can$18.00
Jack & Jones
Signature waist trunk Can$18.00
Jack & Jones
Signature waist trunk Can$18.00
Jack & Jones
Neon dot trunk Can$18.00
Jack & Jones
Logo waist trunk Can$18.00
Jack & Jones
Heathered trunk Can$38.00
Bluebuck
Heathered trunk Can$38.00
Bluebuck
Heathered trunk Can$38.00
Bluebuck
Modal trunk Can$34.00
Calvin Klein
Editor's pick
Slim fit trunk Can$32.00
JM
New
XOXO trunk Can$32.00
Diesel
Modal jersey trunk Can$20.00 Can$9.99
Le 31
Band modal trunk Can$20.00 Can$9.99
Le 31
Modal jersey trunk Can$20.00 Can$9.99
Le 31
New
Space-dye denim trunk Can$20.00
Le 31
Dotwork trunk Can$20.00 Can$12.99
Le 31
Denim mesh trunk Can$20.00 Can$12.99
Le 31
Fireworks trunk Can$34.00
2(x)ist
Editor's pick
Striped trunk Can$34.00
Saxx
Beer pong trunk Can$34.00
Saxx
Blue stripe trunk Can$35.00
Paul Smith
Life on Mars trunk Can$35.00
Paul Smith
Teal cheetah trunk Can$35.00
Paul Smith
Pop molecule trunk Can$35.00
Paul Smith
Multi-logo trunk Can$55.00
Emporio Armani
Eagle logo trunk Can$55.00
Emporio Armani
Spatial pop trunk Can$36.00
Pump!
NFL trunk Can$36.00
Pump!
Optical neon trunk Can$39.00
C-in2
Pastel mesh trunk Can$39.00
C-in2
Printed trunk Can$29.00 Can$9.99
Le 31
Tricolour trunk Can$20.00 Can$9.99
Le 31
Buffalo waist trunk Can$36.00 Can$19.99
Calvin Klein
Second-skin two-tone trunk Can$36.00 Can$25.95
Calvin Klein

Boxers briefs

Editor's pick
Editor's pick
Editor's pick
Editor's pick
Mesh-like waist boxer brief Can$36.00
Calvin Klein
Editor's pick
Mesh-like waist boxer brief Can$36.00
Calvin Klein

Boxers and briefs that meet your comfort and style expectations


Whether you're working your way downtown, working out at the gym, or simply working through the daily grind, you're always on the move. Your clothing should be versatile enough to accommodate this constant motion, so it's important to make comfort a priority when choosing undergarments, which play a pivotal role in any ensemble. Boxers, briefs, or boxer briefs—whatever your preference, Simons' extensive collection provides many options for you to find styles that will be an asset to your wardrobe. After all, every strong style statement starts with the basics. 

Fun, function, and comfort


The essential boxers for your ensemble should ensure that you have ultimate comfort. Choose from numerous top-quality brands including Calvin Klein, SAXX, and our very own Le 31 label. Whichever brand you go for, it's important to find underwear that fits your function. You can go classic, for example, with Calvin Klein's cotton boxer briefs that offer all-day support. But don't think that boxers and briefs are strictly functional. Express your inner fun and creativity with bright patterns, get creative with boxers with food design prints or try out styles in bright colours, exotic patterns, and eye-catching waistband detailing. 

Which style suits you best?


First you need to ask yourself: are you a boxers or briefs man? Choose boxers in a breathable fabric—such as cotton, modal or bamboo rayon—if you want a comfortable, relaxed fit that gives you more freedom of leg movement. Briefs are designed to be more form fitting, which means they're good for a structured and supported fit—and ideal for exercise. If you're looking to enjoy the best of both worlds, try boxer briefs. Sometimes referred to as trunks, this hybrid design first emerged in the early 1990s and has since grown to become one of the most popular styles of men's underwear.  

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