Underwear - masculine underwear & loungewear

Men's Underwear

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3 for $34.95

Striped microfibre trunk US$19.00
3 for $34.95
Le 31
Recycled microknit trunk US$19.00
3 for $34.95
Le 31
Recycled micro nylon trunk US$19.00
3 for $34.95
Le 31
Microfibre jacquard trunk US$19.00
3 for $34.95
Le 31
Recycled nylon dotted trunk US$19.00
3 for $34.95
Le 31
Aqua jacquard trunk US$19.00
3 for $34.95
Le 31
Trimmed houndstooth trunk US$19.00
3 for $34.95
Le 31
Aqua jacquard brief US$19.00
3 for $34.95
Le 31
Trimmed houndstooth brief US$19.00
3 for $34.95
Le 31

New

Recycled microknit brief US$19.00
3 for $34.95
Le 31

New

Recycled micro nylon brief US$19.00
3 for $34.95
Le 31
Micro nylon dotwork brief US$19.00
3 for $34.95
Le 31

Most popular trunks

Most popular boxer briefs

Most popular briefs

Essential microfibre brief US$35.00
Calvin Klein
NFL jockstrap US$25.00
Pump!

Most popular multi-packs

Most popular tanks & T-shirts

3 for $34.95

Jacquard microfibre brief US$19.00
3 for $34.95
Le 31
Striped microfibre brief US$19.00
3 for $34.95
Le 31

Trunks

Editor's pick

Bright microfibre trunk $15.00 US$9.99
Le 31
Leopard trunk US$19.00
Le 31

Editor's pick

Slim fit trunk US$30.00
JM
Solid bamboo rayon trunk $30.00 US$19.99
Bamboo Underwear
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
Pop foliage trunk US$19.00
Jack & Jones
Geo lettering trunk US$19.00
Jack & Jones
Optical dot trunk US$19.00
Jack & Jones
Optical dot trunk US$19.00
Jack & Jones
Geo lettering trunk US$19.00
Jack & Jones
CK1 multi-logo trunk US$20.00
Calvin Klein
Modal trunk US$30.00
Calvin Klein
Essential microfibre trunk US$35.00
Calvin Klein

New

Solid croc trunk US$20.00
Lacoste

New

Dress up puppies trunk US$30.00
Paul Smith

New

Pop Art trunk US$30.00
Paul Smith

New

Balloon signs trunk US$30.00
Paul Smith

New

Pop stripe trunk US$30.00
Paul Smith

New

Alphabet confetti trunk US$30.00
Paul Smith
Retro stripe boxer brief US$30.00
Paul Smith

New

Teal stripe trunk US$30.00
Paul Smith
Teddy Bear trunk US$99.00
Moschino
Eagle logo trunk US$50.00
Emporio Armani

New

Iconic trunk
3-pack
US$50.00
Lacoste
Croc trunk
3-pack
US$45.00
Lacoste

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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