Underwear - masculine underwear & loungewear

Men's Underwear

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3 for $34.95

Most popular trunks

Editor's pick

Colourful bamboo rayon trunk Can$15.00
Le 31

Editor's pick

Organic cotton solid trunk Can$9.99
Le 31
Treats trunk Can$20.00
Le 31

Most popular boxer briefs

Most popular briefs

Most popular multi-packs

Most popular boxers

New

Seaside loose boxer Can$25.00
Le 31

New

Seaside loose boxer Can$25.00
Le 31

Most popular tanks & T-shirts

Trunks

Organic cotton namesake trunk $20.00 Can$12.99
Le 31
Neon hawaiian trunk Can$15.00
Jack & Jones
Tropical trunk Can$15.00
Jack & Jones

New

Bright colour trunk Can$15.00
Jack & Jones
Logo belt trunk Can$15.00
Jack & Jones
Logo waist trunk Can$15.00
Jack & Jones
Signature waist trunk Can$15.00
Jack & Jones
Signature waist trunk Can$15.00
Jack & Jones
Modal trunk Can$34.00
Calvin Klein

New

Twin-stripe trunk Can$48.00
BOSS
Move trunk Can$48.00
BOSS

Editor's pick

Slim fit trunk Can$32.00
JM
Pastel dot trunk Can$35.00
Paul Smith
Dalmatian trunk Can$35.00
Paul Smith
Multicolour stripe trunk Can$35.00
Paul Smith
NFL trunk Can$36.00
Pump!
Croc sketch trunk Can$59.00
Lacoste
CK1 trunk
3-pack
Can$58.00
Calvin Klein
Metallic trunk
3-pack
Can$68.00
Calvin Klein
CK1 trunk
3-pack
Can$58.00
Calvin Klein

Boxer briefs

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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