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Multi-Buy Promotion

New
Nocturnal foliage trunk US$19.00
3 for $29.95
Jack & Jones
New
Festive party trunk US$19.00
3 for $29.95
Jack & Jones
New
Festive party trunk US$19.00
3 for $29.95
Jack & Jones
Signature waist trunk US$19.00
3 for $29.95
Jack & Jones
Neon dot trunk US$19.00
3 for $29.95
Jack & Jones
New
Festive party trunk US$19.00
3 for $29.95
Jack & Jones
Neon dot trunk US$19.00
3 for $29.95
Jack & Jones
Signature waist trunk US$19.00
3 for $29.95
Jack & Jones
Logo waist trunk US$19.00
3 for $29.95
Jack & Jones

Most popular boxers trunks

Loft trunk US$19.00 US$12.99
Le 31
Leopard trunk US$19.00
Le 31
Editor's pick
Bamboo rayon trunk US$15.00
Le 31

Most popular boxers briefs

Editor's pick
Editor's pick
Editor's pick
1981 boxer brief US$30.00
Calvin Klein
1981 boxer brief US$30.00
Calvin Klein

Most popular slips

Dotted brief US$19.00 US$12.99
Le 31
New

Most popular multi-packs

Editor's pick
Playful pattern trunk
2-pack
US$25.00 US$19.99
Le 31
Editor's pick
Playful pattern trunk
2-pack
US$25.00 US$19.99
Le 31
Editor's pick
Playful pattern trunk
2-pack
US$25.00 US$19.99
Le 31

Most popular tanks & T-shirts

Trunks

Editor's pick
Bamboo rayon trunk US$15.00
Le 31
Accent logo waist trunk US$20.00 US$14.99
Diesel
Athletic-stripe floral trunk US$19.00 US$14.99
Le 31
Arcade trunk US$19.00 US$12.99
Le 31
Micro chalet patterned trunk US$19.00 US$12.99
Le 31
Signature waist trunk US$19.00
3 for $29.95
Jack & Jones
Signature waist trunk US$19.00
3 for $29.95
Jack & Jones
Logo waist trunk US$19.00
3 for $29.95
Jack & Jones
Neon dot trunk US$19.00
3 for $29.95
Jack & Jones
Neon dot trunk US$19.00
3 for $29.95
Jack & Jones
Heathered trunk US$30.00
Bluebuck
Heathered trunk US$30.00
Bluebuck
Heathered trunk US$30.00
Bluebuck
Second-skin two-tone trunk US$30.00
Calvin Klein
New
Buffalo waist trunk US$30.00
Calvin Klein
Essential microfibre trunk US$35.00
Calvin Klein
Modal trunk US$30.00
Calvin Klein
Editor's pick
Slim fit trunk US$30.00
JM
Tricolour trunk US$19.00 US$12.99
Le 31
Chain stripe trunk US$19.00 US$9.99
Le 31
Dotwork trunk US$19.00 US$12.99
Le 31
Denim mesh trunk US$19.00 US$12.99
Le 31
New
Fireworks trunk US$30.00
2(x)ist
Editor's pick
Striped trunk US$30.00
Saxx
Beer pong trunk US$30.00
Saxx
Cheetah trunk US$30.00
Paul Smith
Biker rabbit trunk US$30.00
Paul Smith
Colorful striped trunk US$30.00
Paul Smith
Mixed stripe trunk US$30.00
Paul Smith
Blue stripe trunk US$30.00
Paul Smith
Life on Mars trunk US$30.00
Paul Smith
Teal cheetah trunk US$30.00
Paul Smith
Pop molecule trunk US$30.00
Paul Smith
Multi-logo trunk US$45.00
Emporio Armani
Eagle logo trunk US$45.00
Emporio Armani

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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