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Boxers & Briefs

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Most popular boxers trunks

Artistic fauna trunk Can$20.00 Can$12.99
Le 31

Most popular boxers briefs

Iconic logo boxer brief Can$28.00
Tommy Hilfiger
Retro 1985 boxer brief Can$28.00
Tommy Hilfiger

Most popular multi-packs

Accent seam trunk
2-pack
Can$30.00 Can$19.99
Le 31
Signature boxer brief
2-pack
Can$40.00 Can$29.95
Tommy Hilfiger

3 for 29.95$

New
North Pole trunk Can$18.00
3 for 29.95$
Jack & Jones
New
North Pole trunk Can$18.00
3 for 29.95$
Jack & Jones
Logo waist trunk Can$18.00
3 for 29.95$
Jack & Jones

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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