Underwear - masculine underwear & loungewear

Men's Underwear

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Most popular trunks

Editor's pick

Solid bamboo rayon trunk $35.00 Can$19.99
Bamboo Underwear

Editor's pick

Solid bamboo rayon trunk $35.00 Can$19.99
Bamboo Underwear

Editor's pick

Solid bamboo rayon trunk $35.00 Can$19.99
Bamboo Underwear

Editor's pick

Bright microfibre trunk $15.00 Can$9.99
Le 31

Editor's pick

Organic cotton solid trunk Can$9.99
Le 31

Most popular boxer briefs

New

Repeat logo boxer brief Can$22.00
Champion

New

Repeat logo boxer brief Can$22.00
Champion

Most popular briefs

Most popular multi-packs

Most popular tanks & T-shirts

Trunks

Treats trunk Can$20.00
Le 31
Treats trunk Can$20.00
Le 31
Treats trunk Can$20.00
Le 31

New

Joys of winter trunk Can$18.00
Only & Sons

New

Joys of winter trunk Can$18.00
Only & Sons

New

Joys of winter trunk Can$18.00
Only & Sons
Leopard trunk Can$20.00
Le 31

New

Hunter check trunk Can$20.00
Le 31
Arcade trunk Can$20.00
Le 31

Editor's pick

Slim fit trunk Can$32.00
JM
Signature waist trunk Can$18.00
Jack & Jones
Signature waist trunk Can$18.00
Jack & Jones
Logo waist trunk Can$18.00
Jack & Jones
Pop foliage trunk Can$18.00
Jack & Jones
Optical dot trunk Can$18.00
Jack & Jones
Solid croc trunk Can$25.00
Lacoste
Solid croc trunk Can$25.00
Lacoste
Essential microfibre trunk Can$42.00
Calvin Klein
Modal trunk $34.00 Can$24.95
Calvin Klein
Modal trunk $34.00 Can$24.95
Calvin Klein

New

Wolf mosaic trunk Can$29.00
Saxx

New

Contrast waist trunk Can$26.00
Diesel

New

Move trunk Can$48.00
BOSS
Pop tiger trunk Can$42.00
BOSS
Dress up puppies trunk Can$35.00
Paul Smith
Pop Art trunk Can$35.00
Paul Smith
Balloon signs trunk Can$35.00
Paul Smith
Pop stripe trunk Can$35.00
Paul Smith
Alphabet confetti trunk Can$35.00
Paul Smith
Teal stripe trunk Can$35.00
Paul Smith
Retro stripe boxer brief Can$35.00
Paul Smith
NFL trunk Can$36.00
Pump!
Teddy Bear trunk Can$125.00
Moschino
Eagle logo trunk Can$60.00
Emporio Armani
Motion trunk
3-pack
Can$58.00
Lacoste
Metallic trunk
3-pack
Can$68.00
Calvin Klein
CK1 trunk
3-pack
Can$58.00
Calvin Klein
Bright trunk
3-pack
Can$50.00
Diesel

New

Infrared trunk 2-pack Can$57.00
HUGO

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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