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Underwear - masculine underwear & loungewear
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Trunks

Pastel mesh trunk Can$39.00
C-in2
Tricolour trunk Can$20.00 Can$9.99
Le 31
Loft trunk Can$20.00 Can$9.99
Le 31

Boxers briefs

Essential ribbed boxer brief Can$20.00
3 for $29.95
Le 31
Editor's pick
Mesh-like waist boxer brief Can$36.00 Can$25.95
Calvin Klein
Editor's pick
Mesh-like waist boxer brief Can$36.00 Can$25.95
Calvin Klein
1981 boxer brief Can$36.00 Can$25.95
Calvin Klein
Editor's pick
'90s logo boxer brief
2-pack
Can$38.00 Can$29.95
Calvin Klein

Briefs

Nautical stripe brief Can$20.00
3 for $29.95
Le 31
Space-dye denim brief Can$20.00
3 for $29.95
Le 31
Iridescent-stripe modal brief Can$20.00
3 for $29.95
Le 31
Trimmed houndstooth brief Can$20.00
3 for $29.95
Le 31
Heather stripe brief Can$20.00
3 for $29.95
Le 31
Essential ribbed brief Can$20.00
3 for $29.95
Le 31
Prince of Wales brief Can$20.00
3 for $29.95
Le 31
Editor's pick
Micro modal brief Can$25.00
JM
Editor's pick
Micro modal brief Can$25.00
JM
Essential microfibre brief Can$38.00
Calvin Klein
Mini-stripe modal thong Can$35.00
Gregg Homme
Wonder microfibre thong Can$25.00
Gregg Homme
Mini stripe modal brief Can$39.00
Gregg Homme
Wonder microfibre brief Can$41.00
Gregg Homme
Heathered brief Can$36.00
Bluebuck
Heathered brief Can$36.00
Bluebuck
Neon logo brief Can$32.00
C-in2

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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