Underwear - masculine underwear & loungewear

Men's Underwear

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Most popular boxers trunks

Editor's pick

Bright microfibre trunk $15.00 Can$9.99
Le 31
Organic cotton tropical trunk $20.00 Can$12.99
Le 31
Dotwork trunk $20.00 Can$12.99
Le 31

Most popular boxers briefs

Editor's pick

Bright jersey boxer brief Can$9.99
Humör

Editor's pick

Bright jersey boxer brief Can$9.99
Humör

Editor's pick

Bright jersey boxer brief Can$9.99
Humör

Most popular slips

Dotted brief $20.00 Can$12.99
Le 31

Most popular multi-packs

Most popular tanks & T-shirts

Essential tank Can$20.00
Le 31
Lounge logo T-shirt Can$80.00
Emporio Armani

Trunks

Metal texture trunk $20.00 Can$12.99
Le 31
Aqua jacquard trunk Can$20.00
Le 31
Leopard trunk Can$20.00
Le 31
Slanted logo trunk $25.00 Can$14.99
Diesel

Editor's pick

Slim fit trunk Can$32.00
JM

Editor's pick

Slim fit trunk Can$32.00
JM

Editor's pick

Slim fit trunk Can$32.00
JM
Solid bamboo rayon trunk $35.00 Can$19.99
Bamboo Underwear
Signature waist trunk Can$18.00
Jack & Jones
Logo waist trunk Can$18.00
Jack & Jones
Pop foliage trunk Can$18.00
Jack & Jones
Music lover trunk Can$18.00
Jack & Jones
Geo lettering trunk Can$18.00
Jack & Jones
Optical dot trunk Can$18.00
Jack & Jones
CK1 multi-logo trunk Can$26.00
Calvin Klein
CK1 minimalist trunk $38.00 Can$24.95
Calvin Klein
CK1 repeat logo trunk $38.00 Can$24.95
Calvin Klein
Essential microfibre trunk Can$42.00
Calvin Klein
Modal trunk Can$34.00
Calvin Klein
Logo-trim trunk $32.00 Can$24.95
Tommy Hilfiger
Retro stripe boxer brief Can$35.00
Paul Smith
CK1 trunk
3-pack
Can$58.00
Calvin Klein
Metallic trunk
3-pack
Can$68.00
Calvin Klein

Boxers briefs

New

OG boxer brief Can$39.00
Stance

New

Pau boxer brief Can$33.00
Stance

New

Curren boxer brief Can$33.00
Stance

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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