FREE DELIVERY: Get ready to celebrate! Free delivery in store and by mail on orders of $100 or more | Free returns* satisfaction guaranteed
star-rounded Search by image
Back to men
Underwear - masculine underwear & loungewear
Men>Underwear & Leisurewear>New>

Boxers & Briefs

Sort by: New   Price   Most popular
Zoom   Page 1 of 2   31 items   View all
Wheelie boxer brief Can$25.00
Poches & fils
Eggseuse my french boxer brief Can$25.00
Poches & fils
Such a tool boxer brief Can$25.00
Poches & fils
Eggplant boxer brief Can$25.00
Poches & fils
E.T. boxer brief Can$15.00
North Pole trunk Can$18.00
3 for 29.95$
Jack & Jones
Geo pattern trunk Can$33.00
Accent red brief Can$33.00
Red trunk Can$39.00
Blue accent striped trunk Can$18.00
3 for 29.95$
Jack & Jones
Graffiti logo trunk Can$37.00 Can$19.99
Calvin Klein
Geo camo trunk Can$37.00 Can$19.99
Calvin Klein
Multi-logo trunk Can$34.00 Can$24.95
Calvin Klein

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.  


Welcome to!

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 FREE delivery for a limited time in the 48 contiguous states.