Underwear - masculine underwear & loungewear

Men's Underwear

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Most popular trunks

Solid croc trunk $20.00 US$14.99
Lacoste
Solid croc trunk $20.00 US$14.99
Lacoste

Most popular boxer briefs

Multi-logo boxer brief $20.00 US$14.99
Champion
Multi-logo boxer brief $20.00 US$14.99
Champion
Multi-logo boxer brief $20.00 US$14.99
Champion
Heathered jersey boxer brief $20.00 US$14.99
Champion
Repeat logo boxer brief $22.00 US$14.99
Champion
Repeat logo boxer brief $22.00 US$14.99
Champion

Most popular briefs

Most popular multi-packs

Most popular boxers

Most popular tanks & T-shirts

Trunks

Treats trunk US$19.00
Le 31
Treats trunk US$19.00
Le 31
Treats trunk US$19.00
Le 31
Joys of winter trunk US$19.00
Only & Sons
Joys of winter trunk US$19.00
Only & Sons
Joys of winter trunk US$19.00
Only & Sons
Arcade trunk US$19.00
Le 31

Editor's pick

Slim fit trunk US$30.00
JM

Editor's pick

Slim fit trunk US$30.00
JM

Editor's pick

Solid bamboo rayon trunk $30.00 US$19.99
Bamboo Underwear
Signature waist trunk US$19.00
Jack & Jones
Signature waist trunk US$19.00
Jack & Jones
Logo waist trunk US$19.00
Jack & Jones
Optical dot trunk US$19.00
Jack & Jones
Essential microfibre trunk US$35.00
Calvin Klein
Modal trunk US$30.00
Calvin Klein
Modal trunk US$30.00
Calvin Klein
Modal trunk US$30.00
Calvin Klein
Contrast waist trunk $25.00 US$19.99
Diesel
Contrast waist trunk $25.00 US$19.99
Diesel
Contrast waist trunk $25.00 US$19.99
Diesel
Silly rabbits trunk US$30.00
Paul Smith
Dress up puppies trunk US$30.00
Paul Smith
Pop Art trunk US$30.00
Paul Smith
Balloon signs trunk US$30.00
Paul Smith
Pop stripe trunk US$30.00
Paul Smith
Alphabet confetti trunk US$30.00
Paul Smith
Teal stripe trunk US$30.00
Paul Smith
Colourful polka dot trunk US$30.00
Paul Smith
NFL trunk US$30.00
Pump!
Teddy Bear trunk US$99.00
Moschino
Eagle logo trunk US$50.00
Emporio Armani

Men's Boxers & Briefs

Whether you're working, training at the gym, or simply relaxing at home, comfort is a priority. And when it comes to comfort, choosing the right underwear is key. At Simons, we offer a wide variety of trunks, boxers, and boxer briefs to suit your every need.

 

Take your pick in our selection of high-quality, comfortable, and sometimes playful designs by Calvin Klein, Jack & Jones, BOSS by HUGO BOSS, SAXX, or our private brand, Le 31. Make sure to choose the fabric that's right for you. Your underwear should be stretchy and breathable. Cotton, modal, and bamboo rayon are particularly popular!

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