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Boxers & Briefs

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Most popular boxers trunks

Classic trunk Can$28.00 Can$19.99
G-Star Raw
Food truck trunk Can$20.00 Can$12.99
Le 31
Iconic Hero trunk Can$19.99 Can$15.99
Garden of Eden trunk Can$20.00 Can$9.99
Le 31
Editor's pick
Loft trunk Can$20.00 Can$12.99
Le 31

Most popular boxers briefs

Microfibre boxer brief Can$20.00 Can$12.99
Iron Strength boxer brief Can$36.00
Calvin Klein
E.T. boxer brief Can$15.00

Most popular multi-packs

Signature boxer brief
Can$40.00 Can$29.95
Tommy Hilfiger
Essential trunk
Can$46.00 Can$29.95
Tommy Hilfiger
Pastel accent trunk
Can$40.00 Can$29.95
Blue accent trunk
Can$40.00 Can$29.95
90 logo brief
Calvin Klein

Most popular slips

Sheer stripe brief Can$18.00 Can$9.99
Le 31
Message waist brief Can$18.00 Can$9.99
Le 31
Sporty brief Can$20.00 Can$9.99
Le 31

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, Tommy Hilfiger, 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 or 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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We are happy to now offer shipping to the United States.

Please note that all prices are in Canadian dollars.

Customs duties may apply and are the customer's responsibility.

*Excluding shipping fees and gift cards

Enjoy easy delivery with a flat fee of Can$10.00 for shipping in the 48 contiguous states.