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Featured

+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31
+1
Multi-stripe TENCEL* Modal trunk regular price $25.00 discounted price US$14.99
Le 31

3 for $34.95

Editor's pick

Bright microfibre trunk discounted price US$15.00
3 for $34.95
Le 31

Editor's pick

Bright microfibre trunk discounted price US$15.00
3 for $34.95
Le 31

Editor's pick

Bright microfibre trunk discounted price US$15.00
3 for $34.95
Le 31

3 for $39.95

Bright organic cotton trunk discounted price US$19.00
3 for $39.95
Le 31
Bright organic cotton trunk discounted price US$19.00
3 for $39.95
Le 31
Bright organic cotton trunk discounted price US$19.00
3 for $39.95
Le 31

Most popular trunks

Contrast-line TENCEL* Modal trunk regular price $19.00 discounted price US$14.99
Le 31
Contrast-line TENCEL* Modal trunk regular price $19.00 discounted price US$14.99
Le 31
Contrast-line TENCEL* Modal trunk regular price $19.00 discounted price US$14.99
Le 31
Festive print trunk discounted price US$19.00
Le 31
Foliage trunk discounted price US$19.00
Le 31
Colourful snack trunk discounted price US$19.00
Le 31
Colourful snack trunk discounted price US$19.00
Le 31
Festive print trunk discounted price US$19.00
Le 31
Colourful print TENCEL* Modal trunk discounted price US$19.00
Le 31

Most popular boxer briefs

Mirage boxer brief
VIBE
discounted price US$30.00
Saxx
Earthy boxer brief
VIBE
discounted price US$30.00
Saxx
Nautical stripe boxer brief
VIBE
discounted price US$30.00
Saxx
Mini-stripe boxer brief
VIBE
discounted price US$30.00
Saxx

Editor's pick

Woodland camo boxer brief
VIBE
discounted price US$30.00
Saxx
Butterfly palm boxer brief
VIBE
discounted price US$30.00
Saxx

Most popular briefs

Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31
Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31
Tone-on-tone Feel lyocell brief discounted price US$25.00
Le 31
Navy stripe brief regular price $19.00 discounted price US$14.99
Le 31
Boreal stripe brief regular price $19.00 discounted price US$14.99
Le 31
Contrast stripe brief regular price $19.00 discounted price US$14.99
Le 31

Most popular multi-packs

Solid organic cotton boxer briefs
2-pack
discounted price US$19.99
Le 31
Classic organic cotton boxer briefs
2-pack
discounted price US$19.99
Le 31
Classic stretch cotton boxer briefs
3-pack
discounted price US$45.00
Calvin Klein
Classic microfibre trunks
3-pack
discounted price US$50.00
Calvin Klein
Classic stretch cotton trunks
3-pack
discounted price US$45.00
Calvin Klein
Classic microfibre boxer briefs
3-pack
discounted price US$50.00
Calvin Klein

Most popular boxers

Twin-stripe loose boxer discounted price US$25.00
Le 31
Twin-stripe loose boxer discounted price US$25.00
Le 31
Patterned loose boxer discounted price US$25.00
Le 31

Most popular tanks & T-shirts

Organic cotton V-neck lounge T-shirt
2-pack
discounted price US$24.95
Le 31
Classic ribbed tanks
3-pack
discounted price US$45.00
Calvin Klein
Classic crew-neck T-shirts
3-pack
discounted price US$45.00
Calvin Klein

Trunks

Colour block trunk discounted price US$19.00
Le 31
Colour block trunk discounted price US$19.00
Le 31
Colour block trunk discounted price US$19.00
Le 31
Tone-on-tone Feel Lyocell trunk discounted price US$25.00
Le 31

Editor's pick

Colourful bamboo rayon trunk discounted price US$15.00
Le 31
Striped-waistband microfibre trunk regular price $15.00 discounted price US$9.99
Le 31
Contrast topstitch trunk discounted price US$15.00
Le 31
Sports club trunk discounted price US$19.00
Le 31
Denim-like trunk discounted price US$19.00
Le 31

New

Graded pastel trunk discounted price US$19.00
Le 31
Recycled micro nylon trunk discounted price US$19.00
Le 31
Words of love trunk regular price $19.00 discounted price US$9.99
Le 31
Contrast stripe trunk regular price $19.00 discounted price US$14.99
Le 31
Boreal stripe trunk regular price $19.00 discounted price US$14.99
Le 31
Vertical blue stripe trunk discounted price US$19.00
Le 31
Athletic stripe trunk regular price $19.00 discounted price US$14.99
Le 31
Micro-zigzag trunk regular price $19.00 discounted price US$14.99
Le 31
Hatched stripe trunk discounted price US$19.00
Le 31
Geometric shape trunk discounted price US$19.00
Le 31

New

Two-tone band trunk discounted price US$15.00
Jack & Jones

New

Two-tone band trunk discounted price US$15.00
Jack & Jones

New

Two-tone band trunk discounted price US$15.00
Jack & Jones

New

Two-tone band trunk discounted price US$15.00
Jack & Jones

New

Two-tone band trunk discounted price US$15.00
Jack & Jones

New

Skeleton surfer trunk discounted price US$15.00
Jack & Jones

New

Tropical skull trunk discounted price US$15.00
Jack & Jones

New

Tropical hue trunk discounted price US$15.00
Jack & Jones

New

Tropical hue trunk discounted price US$15.00
Jack & Jones
Surf print band trunk discounted price US$15.00
Jack & Jones
Surf print band trunk discounted price US$15.00
Jack & Jones
Tropical flora trunk discounted price US$15.00
Jack & Jones
Tropical flora trunk discounted price US$15.00
Jack & Jones

New

Exotic-band trunk discounted price US$15.00
Jack & Jones
Tropical flora trunk discounted price US$15.00
Jack & Jones

New

Graphic band trunk discounted price US$15.00
Jack & Jones
Graffiti logo trunk discounted price US$15.00
Jack & Jones
Paradise blue trunk discounted price US$15.00
Jack & Jones
Neon skull trunk discounted price US$15.00
Jack & Jones
Tropical flamingo trunk discounted price US$15.00
Jack & Jones
Neon skull trunk discounted price US$15.00
Jack & Jones
Solid and patterned trunk discounted price US$15.00
Jack & Jones
Logo waist trunk discounted price US$15.00
Jack & Jones
Signature waist trunk discounted price US$15.00
Jack & Jones
Signature waist trunk discounted price US$15.00
Jack & Jones
Bright colour trunk discounted price US$15.00
Jack & Jones
Logo belt trunk discounted price US$15.00
Jack & Jones
Signature waist trunk discounted price US$15.00
Jack & Jones
Monochrome microfibre trunk discounted price US$15.00
Jack & Jones
Signature solid trunk discounted price US$19.00
Guess
Contrast-waist orange trunk discounted price US$19.00
Guess
Contrast-waist orange trunk discounted price US$19.00
Guess
Beer Pong trunk
VIBE
discounted price US$30.00
Saxx
Logo waist solid trunk
VIBE
discounted price US$30.00
Saxx

Editor's pick

Slim fit trunk discounted price US$30.00
JM

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!