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Underwear - masculine underwear & loungewear
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Most popular boxers trunks

Editor's pick
Get Lucky trunk US$19.00 US$12.99
Le 31

Most popular boxers briefs

Editor's pick
Editor's pick
Editor's pick

Most popular slips

Most popular multi-packs

Most popular tanks & T-shirts

Trunks

New
Modal striped trunk US$19.00
Le 31
International boxer brief US$19.00 US$9.99
Le 31
New
Modal striped trunk US$19.00
Le 31
Treats trunk US$19.00 US$12.99
Le 31
New
Exotic bamboo trunk US$19.00
Le 31
Leopard trunk US$19.00
Le 31
New
Rugby boxer brief US$19.00
Le 31
Micro chalet patterned trunk US$19.00 US$12.99
Le 31
New
Heather stripe trunk US$19.00
Le 31
Starry organic cotton trunk US$19.00 US$12.99
Le 31
Signature waist trunk US$19.00
Jack & Jones
Neon dot trunk US$19.00
Jack & Jones
Logo waist trunk US$19.00
Jack & Jones
Heathered trunk US$30.00
Bluebuck
Heathered trunk US$30.00
Bluebuck
Heathered trunk US$30.00
Bluebuck
Modal trunk US$30.00
Calvin Klein
Editor's pick
Slim fit trunk US$30.00
JM
XOXO trunk US$30.00
Diesel
Solid bamboo trunk US$30.00
Bamboo Underwear
Solid bamboo trunk US$30.00
Bamboo Underwear
New
Linear trunk US$30.00
Paul Smith
New
Figurative heart trunk US$30.00
Paul Smith
New
Confetti rabbit trunk US$30.00
Paul Smith
Pastel mesh trunk US$35.00
C-in2
Tricolour trunk US$19.00 US$9.99
Le 31
Loft trunk US$19.00 US$9.99
Le 31
Combined stripe trunk US$30.00 US$14.99
Saxx
Pop molecule trunk US$30.00 US$14.99
Paul Smith
Life on Mars trunk US$30.00 US$14.99
Paul Smith
Teal cheetah trunk US$30.00 US$14.99
Paul Smith
Editor's pick
Playful pattern trunk
2-pack
US$25.00 US$19.99
Le 31
CK modal trunk
3-pack
US$55.00
Calvin Klein
Metallic trunk
3-pack
US$55.00
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, 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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